Water → HCID 89701795、化合物

HRID 2280676ノート

反応式

HRID 2280676 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[C:13]([CH3:28])=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[CH:21]=2)[C:15]([CH3:19])=[CH:16][C:17]=1O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[F:11][C:12]1[C:13]([CH3:28])=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[CH:21]=2)[C:15]([CH3:19])=[CH:16][C:17]=1[O:5][C@H:6]1[CH2:10][CH2:9][O:8][CH2:7]1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 58248246HCID 58248246、化合物HCID 89701791HCID 89701791、化合物

生成物 1

HCID 89701795HCID 89701795、化合物収率 50.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

The crude (R)-tetrahydrofuran-3-yl methanesulfonate 1b (202 mg, 1.22 mmol), the crude 3-fluoro-3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-ol 19b (200 mg, 0.81 mmol) and cesium carbonate (527 mg, 1.62 mmol) were dissolved in 5 mL of N,N-dimethylformamide. The reaction mixture was heated to 80° C. and stirred for 12 hours. The resulting mixture was mixed with 20 mL of water and extracted with ethyl acetate (30 mL×2). The combined organic phase was washed with water (30 mL) and saturated sodium chloride solution (30 mL) successively, dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system B to obtain the title compound (S)-(3′-fluoro-2′,6′-dimethyl-4′-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol 19c (130 mg, yield 50.8%) as a colorless slime.

後処理

  1. extractionextracted with ethyl acetate (30 mL×2)
  2. washThe combined organic phase was washed with water (30 mL) and saturated sodium chloride solution (30 mL) successively
  3. dry with materialdried with anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography with elution system B

出典と根拠

ORDレコード
ord-3c062bbccbee4ce3bcfea134c23f7eff
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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