Sodium hydride → Ethyl 5-methyl-2-heptenoate

Temperature

0 °C

Sodium hydride (60% dispersion, 2.4 g, 65 mmol) was washed with hexane and suspended in dimethoxyethane 60 mL. While cooling in ice water bath triethyl phosphonoacetate was slowly added, calcd. 5 minutes. The reaction was stirred for 15 minutes at 0° C. and a solution of 3-methyl-1-pentanal 11 (6.5 g, 65 mmol) in imethoxyethane 20 mL was added. After refluxing overnight, it was concentrated, water and hexane were added, the organic phase was separated, and the aqueous portion discarded. The solution was washed twice with brine and dried on magnesium sulfate. The solvent was evaporated to give 12 (6.75 g, 61%). 1H-NMR (CDCl3) δ 6.89 (m, 1H, —CH2CH:CHCOOEt), 5.77 (d, 1H, —CH2CH:CHCOOEt), 4.16 (q, 2H, —COOCH2CH3), 2.15 and 1.98 (1H each and a multiplet, —CH2CH:CHCOOEt), 1.48 (m, 1H, C2H5(CH3)CHCH2), 1.30–1.10 (m), and 0.83.

1. additionwas slowly added
2. custom5 minutes
3. temperatureAfter refluxing overnight
4. concentrationit was concentrated
5. additionwater and hexane were added
6. customthe organic phase was separated
7. washThe solution was washed twice with brine
8. customdried on magnesium sulfate
9. customThe solvent was evaporated

ORD record

ord-11065c0c4e1144e4a32b925e806e350f

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07164034B2