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Tetrahedron Letters

Volumn 32, Issue 49, 1991, Pages 7165-7166

A simple method for the microscale preparation of mosher's acid chloride

(2) Ward, Dale E a Rhee, Chung K a

a UNIVERSITY OF SASKATCHEWAN (Canada)

Author keywords

microscale; Mosher's acid; Mosher's acid chloride; Mosher's esters; preparation of acid chlorides

Indexed keywords

MOSHERS ACID; PHENYLACETIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0026040063 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(91)80466-J Document Type: Article

Times cited : (180)

References (21)

1
- 0010640653
- (1969) J. Org. Chem. , vol.34 , pp. 2543
- Dale¹ Dull² Mosher³

2
- 33947085552
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 512
- Dale¹ Mosher²

3
- 0000002768
- J.D. Morrison, Academic Press, New York
- (1983) In Asymmetric Synthesis , vol.1 , pp. 125-142
- Yamaguchi¹

4
- 0025061098
- (1990) Tetrahedron Lett. , vol.31 , pp. 75
- Jeanneret-Gris¹ Pousaz²

5
- 84918611641
- For an alternative method see footnote 1 in ref. 2.

6
- 84984085993
- Eine Methode zur katalysierten Herstellung von Carbons�ure- und Sulfos�ure-chloriden mit Thionylchlorid
- (1959) Helvetica Chimica Acta , vol.42 , pp. 1653
- Bosshard¹ Mory² Schmid³ Zollinger⁴

7
- 84987487698
- Improved Modification of the Rosenmund Reduction
- (1976) Synthesis , pp. 767
- Burgstahler¹ Weigel² Schaefer³

8
- 84943498834
- Eine einfache Veresterungsmethode im Eintopf-Verfahren
- (1978) Helvetica Chimica Acta , vol.61 , pp. 1675
- Stadler¹

9
- 0001452427
- (1978) J. Org. Chem. , vol.43 , pp. 3972
- Wissner¹ Grudzinskas²

10
- 0000865362
- (1983) Tetrahedron Lett. , vol.24 , pp. 1543
- Fujisawa¹ Mori² Tsuge³ Sato⁴

11
- 0000271348
- REDUCTION OF CARBOXYLIC ACIDS TO ALDEHYDES: 6-OXODECANAL
- (1988) Organic Syntheses , vol.66 , pp. 121
- Fujisawa¹ Sato²

12
- 84918617356
- 1H NMR spectrum shows signals for MTPAC1, various amounts of MTPA [δ 3.57 (3H, q)] and singlets at δ 8.05, 3.01, 2.93, and 1.93.
- (1978) th , pp. 478
- Paasivirta¹ Ahonen² Hakli³

13
- 84918635489
- For a discussion of the NMR spectrum of DMFCl and its hydrolysis products see:
- (1976) Chem. Abstr. , vol.93 , pp. 238638j

14
- 37049098233
- Factors in the formation of isomerically and optically pure alkyl halides. Part XI. Vilsmeier reagents for the replacement of a hydroxy-group by chlorine or bromine
- (1976) Journal of the Chemical Society, Perkin Transactions 1 , pp. 754
- Hepburn¹ Hudson²

15
- 84989453187
- General Method for the Formylation of Alcohols with Dimethylformamide: An Extension of the Vilsmeier-Haack Reaction
- (1985) Synthesis , pp. 426
- Barluenga¹ Campos² Gonzalez-Nuñez³ Asensio⁴

16
- 84918653659
- 3)] when using < 0.01 equivalents of DMF. iii) On a 0.02 mmol scale, 0.15 mg or 0.16 μL = 0.002 mmol of DMF; adding this amount reliably presents additional experimental difficulty.

17
- 84918652589
- 1H NMR).

18
- 84918606429
- We have prepared up to 50 mg of MTPACl using this procedure. Similarly, phenylacetyl chloride was prepared in 95% yield on a 1 mmol scale.

19
- 84918618561
- The procedure tolerates wide variation in stoichiometry. As long as oxalyl chloride is present in excess, analogous results were obtained using 0.1, 0.25, 1.0 or 10 equivalents of DMF.

20
- 84918643082
- Pyridine or pyridine with DMAP can also be used as base, however, the reaction is slower. Success on this scale requires dry solvent, reagents, and glassware.

21
- 84918603984
- Obviously, complete conversion is important for accurate measurement of ee. The rate constant for formation of the (R,R) diastereomer is ca. 1.5-2 times that for the (S,R) diastereomer.

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