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

HRID 2377612Notes

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, 1 H); 5.01 (d, 1 H); 4.93 (d, 1 H); 3.33 (d, 2 H); 2.03 (m, 2 H); 1.34 (m, 2 H); 0.89 (m, 6 H) 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-8952e99c4c774108a3e23f6b3e9bd968
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470664B2

Reaction notes

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