3-Methylbutanal → HCID 86632042, compound

HRID 883747Notes

Reaction equation

HRID 883747 reaction equation
B(C1CCCCC1)C1CCCCC1.[CH3:14][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17].[Zn](CC)CC.[CH:25](=[O:30])[CH2:26][CH:27]([CH3:29])[CH3:28]>>[CH3:28][CH:27]([CH2:26][C@H:25]([OH:30])[CH:17]=[CH:16][C:15]([CH3:19])([CH3:18])[CH3:14])[CH3:29]

Participants

5

Reactant 4

HCID 115523-MethylbutanalHCID 135123,3-Dimethyl-1-butyneHCID 15879360CID 15879360HCID 178418750HCID 178418750, compound

Product 1

HCID 86632042HCID 86632042, compoundYield 86%

Procedure

The product was prepared by General procedure S using 196 mg (1.1 mmol) Cy2BH, 137 μL (1.1 mmol) 3,3-dimethyl-1-butyne, 1.1 mL (2.1 mmol, 2.0 M in hexanes) Et2Zn, 9.6 mg (0.04 mmol) (−)-MIB, and 107 μL (1.0 mmol) isovaleraldehyde. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 86% yield (146 mg, 0.86 mmol). [α]D20=+16.7 (c=3.0, CHCl3, 85% ee); 1H NMR (CDCl3, 500 MHz): δ 0.88 (t, 6H, J=7.0 Hz), 0.97 (s, 9H), 1.26 (m, 1H), 1.43 (m, 1H), 1.50 (br s, 1H), 1.65 (m, 1H), 4.07 (dt, 1H, J=7.0, 6.8 Hz), 5.31 (dd, 1H, J=15.6, 7.2 Hz), and 5.61 (d, 1H, J=15.7 Hz) ppm; 13C{1H} NMR (CDCl3, 1.25 MHz): δ 22.5, 22.9, 24.6, 29.5, 32.5, 46.6, 71.5, 128.1, and 142.6 ppm; IR (neat): 3334, 3013, 2956, 2869, 2354, 2320, 1662, 1466, 1386, 1363, 1308, 1268, 1220, and 1202 cm−1; HRMS-CI m/z 170.1666 [M+; calcd for C11H22O: 170.1671].

Workup

  1. customThe product was prepared by General procedure S
  2. customThe crude product was purified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-29307197e12d4cfb9fe8214e3dfa107e
Source dataset
uspto-grants-2012_08
Patent number
US08236976B2

Reaction notes

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