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

HRID 2098938ノート

反応式

HRID 2098938 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 T19.2 (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 T19.3 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-804c90afb80c4255ac175b039a5cccdc
出典データセット
uspto-grants-2013_05
特許番号
US08450522B2

反応ノート

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