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 methoxyethane 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:CH: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-2d01f35aadee4ef1ace51dc0548772d1

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138542B2