Cesium carbonate → (S)-(4-fluoro-2',6'-dimethyl-4'-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol

HRID 2280672ノート

反応式

HRID 2280672 の反応式
CS([O:5][C@@H:6]1[CH2:10][CH2:9][O:8][CH2:7]1)(=O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:23]([CH3:24])=[CH:22][C:21](O)=[CH:20][C:19]=2[CH3:26])=[CH:14][C:13]=1[CH2:27][OH:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([CH3:26])=[CH:20][C:21]([O:5][C@H:6]3[CH2:10][CH2:9][O:8][CH2:7]3)=[CH:22][C:23]=2[CH3:24])=[CH:14][C:13]=1[CH2:27][OH:28]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 58248246HCID 58248246、化合物HCID 897017694'-Fluoro-3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-ol

生成物 1

HCID 89701765(S)-(4-fluoro-2',6'-dimethyl-4'-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol収率 105.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

The crude (R)-tetrahydrofuran-3-yl methanesulfonate 1b (83 mg, 0.50 mmol), 4′-fluoro-3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-ol 18c (110 mg, 0.45 mmol) and cesium carbonate (293 mg, 0.90 mmol) were dissolved in 2 mL of N,N-dimethylformamide. The reaction mixture was heated to 90° C. and stirred for 12 hours. The resulting mixture was concentrated under reduced pressure, mixed with 10 mL of water and extracted with ethyl acetate (10 mL×3). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (S)-(4-fluoro-2′,6′-dimethyl-4′-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol 18d (150 mg) as a colorless slime, which was directly used in the next step without further purification.

後処理

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additionmixed with 10 mL of water
  3. extractionextracted with ethyl acetate (10 mL×3)
  4. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  5. dry with materialdried with anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-e90bd396ebbc497892c5ca8270281145
出典データセット
uspto-grants-2015_09
特許番号
US09139548B2

反応ノート

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