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

HRID 20698

反応式

HRID 20698 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b5572fcb9d9044329d31676381ddbca5
出典データセット
uspto-grants-2010_06
特許番号
US07745646B2

関連ノート

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