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

HRID 2280672노트

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HRID 2280672 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e90bd396ebbc497892c5ca8270281145
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139548B2

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