تفاعل #1461356

معادلة التفاعل

Sodium hydride

3-methyl-1-pentanal

3-Methyl-1-pentanal

→

12

المردود 122.0%

Ethyl 5-methyl-2-heptenoate

المردود 122.0%

المذيبات

—

ice water

hexane

dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas slowly added
2. 2
   أخرى5 minutes
3. 3
   درجة الحرارةAfter refluxing overnight
4. 4
   تركيزit was concentrated
5. 5
   workup.ADDITIONwater and hexane were added
6. 6
   أخرىthe organic phase was separated
7. 7
   غسيلThe solution was washed twice with brine
8. 8
   أخرىdried on magnesium sulfate
9. 9
   أخرىThe solvent was evaporated

الإجراء التجريبي

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.

المصدر