Diethyl Malonate → 1,3-Diethyl 2-(1-methylbutyl)propanedioate

HRID 373868

반응식

HRID 373868 반응식
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[O-]CC.[Na+:16].Br[CH:18]([CH2:20][CH2:21][CH3:22])[CH3:19]>C(O)C>[O-:5][CH2:4][CH3:3].[Na+:16].[CH3:19][CH:18]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:20][CH2:21][CH3:22]

참가 물질

7

반응물 4

HCID 7761Diethyl MalonateHCID 78902-BromopentaneHCID 2723922Sodium ethoxideHCID 5360545Sodium

생성물 2

HCID 954491,3-Diethyl 2-(1-methylbutyl)propanedioateHCID 2723922Sodium ethoxide

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
80 °C

실험 절차

Sodium ethoxide was prepared from sodium metal (7.61 g) and absolute ethanol (200 ml). Diethyl malonate (50.3 ml) was added dropwise to the ethanol containing sodium ethoxide. After heating to 80° C., 2-bromopentane (50 g) was added and the mixture was reflued for 24 h. Diethyl (2-pentyl)malonate (62.7 g) was obtained after the usual work-up. Diethyl (2-pentyl)malonate was added to a 50% potassium hydroxide solution and the mixture was heated for 3 h while water/ethanol being distilled off. After cooling, the solution was acidified with concentrated hydrochloric acid. Then, the solution was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the resulting product was heated to 180° C. until bubbling ceased. After distillation, colorless 3R,S-methy-caproic acid was obtained. Yield : 27.7 g (35%), b.p. 200° C./760 mmHg.

출처 및 근거

ORD 기록
ord-287910aea6234a549ae346431ba410ee
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166174

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