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

HRID 20698

Reaktionsgleichung

Reaktionsgleichung von HRID 20698
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b5572fcb9d9044329d31676381ddbca5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745646B2

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