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Synlett

Volumn , Issue 1, 2008, Pages 0137-0141

Efficient solvent-free synthesis of homoallylic alcohols mediated by zinc-copper couple

(4) Zhou, Wenjun a Yan, Wenjun a Wang, Jin Xian a,b Wang, Kehu a

a NORTHWEST NORMAL UNIVERSITY (China)

b LANZHOU UNIVERSITY (China)

Author keywords

Allylation; Homoallylic alcohols; Ketones; Solvent free; Zinc copper couple

Indexed keywords

ALCOHOL; ALLYL COMPOUND; BROMIDE; COPPER; KETONE; SOLVENT; ZINC;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ROOM TEMPERATURE; SYNTHESIS;

EID: 38549131223 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-1000840 Document Type: Article

Times cited : (11)

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- Preparation of the Zinc-Copper Couple: Zinc powder (11.6 g) and distilled H2O (80 mL) were placed into a 100-mL round-bottom flask equipped with a stir bar. With stirring, HCl acid (37, 2 x 1 mL) was added over 10 min. Then the CuSO4 solution (20, 20 mL) was added dropwise with stirring and the stirring was continued for about 15 min. Finally, the mixture was filtered and the solid was washed with H2O (3 x 30 mL, acetone (3 x 10 mL, and Et2O (2 x 10 mL, Then the solid was transferred into a flask equipped with vacuum take-off and dried under vacuum for 3 h at 100°C Other M-Cu couples were also prepared in this way. Preparation of the Homoallylic Alcohols: Zinc-copper couple (0.24 g, allyl bromide (2.5 mmol) and ketones (2 mmol) were placed in a dried round-bottom flask, and the mixture was stirred at r.t. and the reaction was monitored by TLC. After reaction completed, sat. brine (10 mL) was poured into the mixture, th
- 13C NMR and MS.

56
- 38549136357
- Representative Spectroscopic Data for Compounds 3. Compound 3i: IR: 3475, 2976, 1670, 1456, 1269, 1101, 920, 771, 738 cm -1. 1H NMR (400 MHz, CDCl3, δ, 7.24-7.84 (m, 7 H, 5.60-5.70 (m, 1 H, 5.09-5.19 (m, 2 H, 3.88 (q, J, 6.4 Hz, 2 H, 2.65-2.76 (m, 1 H, 2.52-2.63 (m, 1 H, 2.14 (s, 1 H, 1.61 (s, 3 H, 13C NMR (100 MHz, CDCl3, δ, 146.4, 143.3, 143.3, 141.4, 140.2, 133.7, 126.7, 126.5, 125.0, 123.4, 121.5, 119.8, 119.4, 73.8, 48.6, 37.0, 30.1, 26.8. EI-MS: m/z, 250 (2.4, M, 209 (64.9, 193 (16.8, 165 (37.7, 43 (100, 39 (17.2, Anal. Calcd for C 18H18O: C, 86.36; H, 7.25. Found: C, 86.36; H, 7.36. Compound 3p: IR: 3406, 3077, 2977, 1644, 1439, 1372, 1114, 923, 796 cm-1. 1H NMR (400 MHz, CDCl3, δ, 6.88 (d, J, 3.6 Hz, 1 H, 6.63 (d, J, 3.6 Hz, 1 H, 5.67-5.78 (m, 1 H, 5.12-5.19 m
- 2: C, 72.26; H, 8.49. Found: C, 72.28; H, 8.64.

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