Ethyl 2,2-dimethylhex-5-enoate → 2,2-Dimethylhex-5-en-1-ol

HRID 1511557Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([CH3:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[C:9](OCC)=[O:10]>CCOCC>[CH3:7][C:8]([CH3:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:9][OH:10]

Participants

Conditions

Temperature: 22 °C

Procedure

To a stirred solution of 1M LAH in ether (142.14 mL, 142.14 mmol), at 0° C. and under nitrogen, was added dropwise ethyl 2,2-dimethylhex-5-enoate (11.00 g, 64.61 mmol) dissolved in 100 mL anhydrous ether over 1 hour. This reaction solution was stirred at 22° C. for 20 hours, then quenched with water (3 mL), 1M NaOH (11 mL) and water (9 mL), dried over Na2SO4, filtered and concentrated to give the title product (7.22 g, 87.09%). 1H NMR (500 MHz, CDCl3) δ 5.85-5.77 (m, 1H); 5.01 (d, 1H); 4.93 (d, 1H); 3.33 (d, 2H); 2.03 (m, 2H); 1.34 (m, 2H); 0.89 (m, 6H) ppm.

Workup

customquenched with water (3 mL), 1M NaOH (11 mL) and water (9 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-aa5c53fba5f14b629e9ca3488e75c42b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08216999B2

Reaction notes

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