p-Toluenesulfonic acid → 4-(2,3-Difluorophenoxy)-butan-1-ol

HRID 6595

反応式

HRID 6595 の反応式
[F:1][C:2]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C1COCC1.O>[F:1][C:2]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

参加物

5

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 220162562-[4-(2,3-Difluorophenoxy)butoxy]-tetrahydropyran

生成物 1

HCID 220162574-(2,3-Difluorophenoxy)-butan-1-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a solution of 2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran (20) (1 equi.) and commercially available para-toluenesulfonic acid (21) (0.1 equi.) in methanol:THF (1:1) (3 mL/mmole), water (0.005 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (10% EtOAc/hexanes) gave 4-(2,3-difluorophenoxy)-butan-1-ol (22), as a white solid (84%).

後処理

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane (1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (10% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-96173bef1136419e80caf61235bb990a
出典データセット
uspto-grants-2006_08
特許番号
US07083832B2

関連ノート

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