Potassium Carbonate → 4-[[6-[3,4-Dimethoxy-5-(1-methylethyl)phenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl ester

HRID 1494254ノート

反応式

HRID 1494254 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH3:19])=[C:11]([O:20][CH3:21])[CH:10]=1)=[O:8].[CH3:22][O:23][C:24](=[O:36])[C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][CH2:33][CH3:34])[C:26]=1[OH:35].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:22][O:23][C:24](=[O:36])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]2[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH3:19])=[C:11]([O:20][CH3:21])[CH:10]=2)=[O:8])=[C:27]([CH2:32][CH2:33][CH3:34])[C:26]=1[OH:35]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 13019281Methyl 2,4-dihydroxy-3-propylbenzoateHCID 149864006-Bromo-1-[3,4-dimethoxy-5-(1-methylethyl)phenyl]-1-hexanone

生成物 1

HCID 149864154-[[6-[3,4-Dimethoxy-5-(1-methylethyl)phenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl ester収率 98.9%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 6.0 g (0.017 mol) of 6-bromo-1-[3,4-dimethoxy-5-(1-methylethyl)phenyl]-1-hexanone, 3.39 g (0.016 mol) of 2,4-dihydroxy-3-propylbenzoic acid methyl ester and 7.0 g (0.051 mol) of potassium carbonate in 120 mL of acetone and 12 mL of DMF was stirred at reflux for 19 hours. After workup as in Example 16, the crude product was purified by HPLC using 16% ethyl acetate-hexane to give 7.7 g (98% yield) of 4-[[6-[3,4-dimethoxy-5-(1-methylethyl)phenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl ester as an oil. The nmr spectrum was consistent with the structure.

後処理

  1. temperatureat reflux for 19 hours
  2. customAfter workup as in Example 16, the crude product was purified by HPLC

出典と根拠

ORDレコード
ord-3508e699b5c543b0a93b458d4e1bf3c9
出典データセット
uspto-grants-1991_06
特許番号
US05025036

反応ノート

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