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Volumn 36, Issue 4, 2007, Pages 566-567

Di-2-methoxyethyl azodicarboxylate (DMEAD): An inexpensive and separation-friendly alternative reagent for the mitsunobu reaction

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EID: 34248504625 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.566 Document Type: Article

Times cited : (60)

References (18)

1
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- Graduate student from Toyo Kasei Kogyo, Co. Ltd
- Graduate student from Toyo Kasei Kogyo, Co. Ltd.

2
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- O. Mitsunobu, Synthesis 1981, 1;
- (1981) Synthesis , pp. 1
- Mitsunobu, O.¹

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- O. Mitsunobu, M. Yamada, Bull. Chm. Soc. Jpn. 1967, 40, 2380.
- (1967) Bull. Chm. Soc. Jpn , vol.40 , pp. 2380
- Mitsunobu, O.¹ Yamada, M.²

5
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- For reviews, see
- For reviews, see: R. Dembinski, Eur. J. Org. Chem. 2004, 2763;
- (2004) Eur. J. Org. Chem , pp. 2763
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- S. Dandapani, D. P. Curran, Chem. Eur. J. 2004, 10, 3130.
- (2004) Chem. Eur. J , vol.10 , pp. 3130
- Dandapani, S.¹ Curran, D.P.²

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- J. C. Poupon, A. A. Boezio, A. B. Charette, Angew. Chem., Int. Ed. 2006, 45, 1415.
- (2006) Angew. Chem., Int. Ed , vol.45 , pp. 1415
- Poupon, J.C.¹ Boezio, A.A.² Charette, A.B.³

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- T. Y. S. But, P. H. Toy, J. Am. Chem. Soc. 2006, 128, 9636.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 9636
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9
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- A. G. M. Barrett, R. S. Roberts, J. Schroder, Org. Lett. 2000, 2, 2999.
- (2000) Org. Lett , vol.2 , pp. 2999
- Barrett, A.G.M.¹ Roberts, R.S.² Schroder, J.³

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- B. H. Lipshutz, D. W. Chung, B. Rich, R. Corral, Org. Lett. 2006, 8, 5069.
- (2006) Org. Lett , vol.8 , pp. 5069
- Lipshutz, B.H.¹ Chung, D.W.² Rich, B.³ Corral, R.⁴

11
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- N. Rabjohn, Org. Synth. 1955, Coll. 3, 375;
- N. Rabjohn, Org. Synth. 1955, Coll. Vol. 3, 375;

12
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- J. C. Kauer, Org. Synth. 1963, Coll. 4, 411.
- J. C. Kauer, Org. Synth. 1963, Coll. Vol. 4, 411.

13
- 34248532807
- A solution of hydrazine hydrate (15 g, 300 mmol) in 99.5% ethanol (75 mL) was cooled to 5°C with an ice-water bath. 2-Methoxyethyl chloroformate (41.52 g, 300 mmol) was added dropwise in keeping the temperature below 20°C. After 5 min, 2-methoxyethyl chloroformate (41.52 g, 300 mmol) was added simultaneously with a solution of sodium carbonate (31.76 g, 300 mmol) in water (120 mL) below 20°C. After 1 h, the mixture was concentrated under vacuum, and then treated with acetone (100 mL) to precipitate inorganic salts. Filtration, concentration, and purification by recrystallization with a mixture of acetone (75 mL) and toluene (120 mL) gave 50.91 g of a colorless solid (1, 71.9% yield, mp 71.3-76.5°C; Anal. Calcd for C8H 16N2O6: C, 40.68; H, 6.83; N, 11.96, Found: C, 40.88; H, 7.49; N, 12.07, IR (KBr) 1755 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.02 (brs, 2H, 4.27-4.25 m, 4H, 3.58-3.56
- 3) δ 156.59, 70.40, 64.68, 58.69.

14
- 34248595194
- L. A. Carpino, P. J. Crowley, Org. Synth. 1973, Coll. 5, 160.
- L. A. Carpino, P. J. Crowley, Org. Synth. 1973, Coll. Vol. 5, 160.

15
- 34248561453
- To a solution of 1 (45 g, 190.5 mmol) and pyridine (15.09 g, 1.0 equiv, in toluene (450 mL) was added N-bromosuccinimide (37.31 g, 1.1 equiv, slowly at room temperature. After vigorous stirring for 2 h, the reaction mixture was washed with water (180 mL x 2, dried over magnesium sulfate, concentrated under vacuum, and then purified by recrystallization with a mixture of toluene (67.5 mL) and hexane (337.5 mL) to give 39.26 g of DMEAD as yellow prisms (88.0% yield, mp 39.9-40.4°C; Anal. Calcd for C 8H14N2O6: C, 41.03; H, 6.03; N, 11.96, Found: C, 41.09; H, 6.65; N, 11.98, IR (KBr) 1782cm-1; 1H NMR (400 MHz, CDCl3) δ 4.51-4.49 (m, 4H, 3.66-3.63 (m, 4H, 3.32 (s, 6H, 13C NMR (100 MHz, CDCl3) δ 160.04, 69.45, 67.85, 58.84
- 3) δ 160.04, 69.45, 67.85, 58.84.

16
- 34248598992
- Decomposition temperature observed by DSC for DMEAD was 210°C, which is somewhat lower than that of DEAD (227°C by our measurement).
- Decomposition temperature observed by DSC for DMEAD was 210°C, which is somewhat lower than that of DEAD (227°C by our measurement).

17
- 34248563450
- A ratio of (R,R)-2,4-pentanediol, nucleophile, triphenylphosphane, and DMEAD (DIAD) is fixed to be 1/0.85/1/1. All the reactions were carried out at room temperature by addition of one of the azodicarboxylates to a mixture of the other three, except for the case with 4-nitorobenzoic acid that was added at last. The product was isolated by extraction and silica-gel column chromatography.
- A ratio of (R,R)-2,4-pentanediol, nucleophile, triphenylphosphane, and DMEAD (DIAD) is fixed to be 1/0.85/1/1. All the reactions were carried out at room temperature by addition of one of the azodicarboxylates to a mixture of the other three, except for the case with 4-nitorobenzoic acid that was added at last. The product was isolated by extraction and silica-gel column chromatography.

18
- 34248563452
- 2, elution with a mixture of hexane and ethyl acetate = 1/1) was 0.65 for diisopropyl analogue (0.44 for diethyl), while very small 0.08 for 1.
- 2, elution with a mixture of hexane and ethyl acetate = 1/1) was 0.65 for diisopropyl analogue (0.44 for diethyl), while very small 0.08 for 1.

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