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

HRID 20698Notes

Reaction equation

HRID 20698 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b5572fcb9d9044329d31676381ddbca5
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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