Trifluoromethanesulfonic acid → Methyl 2-hydroxy-3-phenylpropanoate

HRID 479758ノート

反応式

HRID 479758 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 518800Methyl 2-hydroxy-3-phenylpropanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-af0467fa14d9463ab0694ddf63829b81
出典データセット
uspto-grants-2003_11
特許番号
US06645989B2

反応ノート

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