Ethyl Acetate → 3-Fluoro-2-(hydroxymethyl)-5-(methylsulfonyl)phenol

HRID 452467ノート

反応式

HRID 452467 の反応式
[F:1][C:2]1[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[C:8]([OH:16])[C:3]=1[C:4](OC)=[O:5].[Li+].[BH4-].CCOC(C)=O>C1COCC1>[F:1][C:2]1[C:3]([CH2:4][OH:5])=[C:8]([OH:16])[CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 66887484Methyl 2-fluoro-6-hydroxy-4-(methylsulfonyl)benzoate

生成物 1

HCID 668875163-Fluoro-2-(hydroxymethyl)-5-(methylsulfonyl)phenol収率 95.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 2-fluoro-6-hydroxy-4-(methylsulfonyl)benzoate (0.14 g, 0.57 mmol) was dissolved in THF (dry) (5 ml). LiBH4 (2M in THF) (0.57 ml, 1.14 mmol) was added dropwise under nitrogen at 0° C. The mixture was allowed to warm to RT and stirred under nitrogen for 45 min. EtOAc was added and the mixture was further quenched with MeOH, then water. The mixture was acidified with 1N HCl and extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to give the crude title compound (0.12 g) 1H-NMR (400 MHz, CD3OD): δ 7.20 (1H, s), 7.16 (1H, dd, J 8.4, 2), δ 4.73 (2H, d, J 1.6), δ 3.10 (3H, s) ppm (J-values are in Hz and shifts relative to solvent-peak at 3.31 ppm).

後処理

  1. customthe mixture was further quenched with MeOH
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6ee9932b9cff4c48ae2eea209764fc2e
出典データセット
uspto-grants-2013_07
特許番号
US08492372B2

反応ノート

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