Diethyl Ether → 2-(3,5-Dimethoxyphenylthio)benzyl alcohol

HRID 1533480ノート

反応式

HRID 1533480 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](O)=[O:15])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[BH4-].[Na+].B(F)(F)F.CCOCC>O1CCCC1>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([S:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[CH2:14][OH:15])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 4311764Sodium borohydrideHCID 110335902-(3,5-Dimethoxyphenylthio)benzoic acid

生成物 1

HCID 118079672-(3,5-Dimethoxyphenylthio)benzyl alcohol収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 12.3 g of the 2-(3,5-dimethoxyphenylthio)benzoic acid, prepared in Example 1, in 50 ml of anhydrous tetrahydrofuran was added 1.8 g of sodium borohydride portionwise at 0° C. After 30 minutes, the resulting solution was treated with 6.3 ml of BF3. Et2O at the same temperature and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and dilute hydrochloric acid, and the ethyl acetate layer was successively washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (eluting solvent; hexane:ethyl acetate=3:1) to give 8.3 g (71%) of a compound of the indicated formula (11).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and dilute hydrochloric acid
  2. washthe ethyl acetate layer was successively washed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography (eluting solvent; hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-69266879ba044211b43788d604b28d67
出典データセット
uspto-grants-2001_03
特許番号
US06207837B1

反応ノート

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