Methanol → Ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate

HRID 563109ノート

反応式

HRID 563109 の反応式
Br[CH:2]([C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([F:23])=[CH:15][CH:14]=1)=[O:12])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C([O-])=[O:25].[Na+].CO>C(OCC)(=O)C>[F:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([C:11](=[O:12])[CH:2]([OH:25])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:14][CH:15]=1

参加物

5

反応物 3

HCID 887MethanolHCID 2723810Sodium FormateHCID 18174722Ethyl 5-bromo-6-(4-fluoro-1-naphthyl)-6-oxohexanoate

生成物 1

HCID 18174704Ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of ethyl 5-bromo-6-(4-fluoro-1-naphthyl)-6-oxohexanoate (34.3 g), sodium formate (34.0 g) and methanol (150 ml) was stirred with heating under reflux for 16 hours. The reaction mixture was diluted with ethyl acetate (500 ml) and washed with water (200 ml×2). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate was obtained as a yellow oil (19.0 g, 65%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

後処理

  1. temperaturewith heating
  2. temperatureunder reflux for 16 hours
  3. washwashed with water (200 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-97a37b0a8dfa46f98ae5fbe2570892a2
出典データセット
uspto-grants-2011_11
特許番号
US08067453B2

反応ノート

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