2-Methyl-2-pentenal → HCID 130776930, compound

HRID 883738Notes

Reaction equation

HRID 883738 reaction equation
[Zn](CC)[CH2:2][CH3:3].[CH3:6][C:7](=[CH:10][CH2:11][CH3:12])[CH:8]=[O:9]>>[CH3:6][C:7](=[CH:10][CH2:11][CH3:12])[C@@H:8]([OH:9])[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 121772-Methyl-2-pentenalHCID 178418750HCID 178418750, compound

Product 1

HCID 130776930HCID 130776930, compoundYield 73%

Procedure

The product was prepared by General procedure L using 1.0 mL (2.0 mmol, 2.0 M in hexanes) Et2Zn, 9.6 mg (0.04 mmol) (−)-MIB, and 114 μL (1.0 mmol) 2-methyl-2-pentenal. The crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 73% yield (93 mg, 0.73 mmol). [α]D20=−5.8 (c=0.73, CHCl3, 95% ee); 1H NMR (CDCl3, 500 MHz) δ 0.77 (t, 3H, J=7.4 Hz), 0.89 (t, 3H, J=7.5 Hz), 1.45-1.49 (m, 2H), 1.51 (s, 3H), 1.61 (br s, 1H), 1.96 (q, 2H, J=7.4 Hz), 3.81 (t, 1H, J=6.7 Hz), and 5.29 (t, 1H, J=6.9 Hz) ppm; 13C {1H} NMR (CDCl3, 125 MHz) δ.10.0, 10.8, 14.0, 20.7, 27.6, 79.4, 128.6, and 136.1 ppm; IR (neat) 3360, 2962, 2932, 2875, 2348, 1722, 1670, 1461, 1376, 1335, 1308, 1261, 1097, 1054, and 1008 cm−1; HRMS-CI m/z 128.1206 [M+; calcd for C8H16O: 128.1201].

Workup

  1. customThe product was prepared by General procedure L
  2. customThe crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a7ab4d2fb03f40649706b690c70f9a58
Source dataset
uspto-grants-2012_08
Patent number
US08236976B2

Reaction notes

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