Trifluoromethanesulfonic acid → Methyl 2-hydroxy-3-phenylpropanoate

HRID 479758노트

반응식

HRID 479758 반응식
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].FC(S(O)(=O)=O)(F)F.ClC(Cl)(Cl)C(=N)O[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:19]([CH:2]([OH:3])[C:1]([O:5][CH3:6])=[O:4])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 62406Trifluoromethanesulfonic acidHCID 66774Methyl GlycolateHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 516892Sodium Bicarbonate

생성물 1

HCID 518800Methyl 2-hydroxy-3-phenylpropanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution containing methyl glycolate (2.5 mL, 32 mmol) and trifluoromethyl-sulfonic acid (150 mL) in CH2Cl2 (10 mL) was added benzyl 2,2,2-trichloro-acetimidate (7.0 mL, 37 mmol). After stirring for several min, the mixture was poured into aqueous NaHCO3 and extracted with Et2O. The organic extract was washed with saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with a solvent gradient of 9-17% EtOAC/Hex to afford the title compound: 1H NMR CDCl3): d 7.34 (m, 5H); 4.62 (s, 2H); 4.11 (s, 2H); 3.78 (s, 3H).

후처리

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with a solvent gradient of 9-17% EtOAC/Hex

출처 및 근거

ORD 기록
ord-af0467fa14d9463ab0694ddf63829b81
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645989B2

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