2'-Fluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid → Methyl 2'-fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate

HRID 1662416ノート

反応式

HRID 1662416 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](O)=[O:15])=[CH:10][C:9]=1[C:17]([O:19][CH3:20])=[O:18]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:11]([CH2:14][OH:15])=[CH:12][CH:13]=1

参加物

3

反応物 1

HCID 577067632'-Fluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid

生成物 1

HCID 57705859Methyl 2'-fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate収率 108.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
23 °C

実験手順

To a stirred solution of 66.32B (0.90 g, 3 mmol) in THF (33 mL) at 0° C. was added borane-THF complex (7 mL, 7 mmol, 1.0M). The reaction was allowed to warm to 23° C. and stirred for 7 hours. The reaction mixture was then concentrated in vacuo. The reaction was diluted with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield 66.32C as a colorless solid (0.850 g, 100% yield).

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionThe reaction was diluted with 1N HCl
  3. extractionextracted three times with EtOAc
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. customthe organic solvent was removed under reduced pressure
  7. customthe product was then purified on silica gel (0-40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-4ff16315cd374508bee4474bfb6c5402
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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