Acetone → (4'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-yl)methanol

HRID 2280670ノート

反応式

HRID 2280670 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH:23]=[O:24])[CH:17]=2)=[C:11]([CH3:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CC(C)=O>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:25])[C:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH2:23][OH:24])[CH:17]=2)=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 897017664'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-carbaldehyde

生成物 1

HCID 89701768(4'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-yl)methanol収率 94%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4′-(Benzyloxy)-4-fluoro-2′,6′-dimethylbiphenyl-3-carbaldehyde 18a (390 mg, 1.17 mmol) were dissolved in 5 mL of methanol, followed by addition of sodium borohydride (66 mg, 1.75 mmol). The reaction solution was stirred for 30 minutes. The resulting solution was mixed with 10 mL of acetone and concentrated under reduced pressure. The residue was 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 (4′-(benzyloxy)-4-fluoro-2′,6′-dimethylbiphenyl-3-yl)methanol 18b (370 mg) as a colorless slime, which was directly used in the next step without further purification.

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was mixed 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-acaeccbf54c1473bbc74de5340aae9ca
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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