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

HRID 452467노트

반응식

HRID 452467 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6ee9932b9cff4c48ae2eea209764fc2e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492372B2

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