Benzene, ((2-bromoethoxy)methyl)- → Ethyl 4-(benzyloxy)-2-(2,3-bis(cyclopentyloxy)-4-methoxybenzoyl)butanoate

HRID 20698노트

반응식

HRID 20698 반응식
[O-][CH2:2]C.[Na+].[CH:5]1([O:10][C:11]2[C:16]([O:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:15]([O:23][CH3:24])[CH:14]=[CH:13][C:12]=2[C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:9][CH2:8][CH2:7][CH2:6]1.Br[CH2:33][CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(O)C>[CH2:36]([O:35][CH2:34][CH2:33][CH:26]([C:25](=[O:31])[C:12]1[CH:13]=[CH:14][C:15]([O:23][CH3:24])=[C:16]([O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:11]=1[O:10][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1)[C:27]([O:29][CH2:30][CH3:2])=[O:28])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

5

반응물 3

HCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 2723922Sodium ethoxideHCID 68742690Methyl 3-(2,3-bis(cyclopentyloxy)-4-methoxyphenyl)-3-oxopropanoate

생성물 1

HCID 68741697Ethyl 4-(benzyloxy)-2-(2,3-bis(cyclopentyloxy)-4-methoxybenzoyl)butanoate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium ethoxide (2.0 g, 29 mmol) was added to a solution of methyl 3-(2,3-bis(cyclopentyloxy)-4-methoxyphenyl)-3-oxopropanoate (11 g, 29 mmol) and ethanol (150 mL) at rt. After refluxing for 1 h, ((2-bromoethoxy)methyl)benzene (12.5 g, 57.8 mmol) was added and refluxing was continued overnight. The reaction was allowed to cool to rt, concentrated, diluted with ethyl acetate (300 mL), and then washed with brine (50 mL×2). The organic layer was dried, filtered, concentrated, and purified by silica gel chromatography (ethyl acetate:petroleum ether) to give ethyl 4-(benzyloxy)-2-(2,3-bis(cyclopentyloxy)-4-methoxybenzoyl)butanoate: MS (ESI): 525.

후처리

  1. temperatureAfter refluxing for 1 h
  2. temperaturerefluxing
  3. concentrationconcentrated
  4. additiondiluted with ethyl acetate (300 mL)
  5. washwashed with brine (50 mL×2)
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (ethyl acetate:petroleum ether)

출처 및 근거

ORD 기록
ord-b5572fcb9d9044329d31676381ddbca5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745646B2

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