Hydrochloric Acid → (+/-)-Ethyl 4-[4-(benzyloxy)phenyl]-2-methyl-2-(methylsulfonyl)butanoate

HRID 533563

반응식

HRID 533563 반응식
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]([S:29]([CH3:32])(=[O:31])=[O:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.IC.Cl>CN(C=O)C>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([CH3:1])([S:29]([CH3:32])(=[O:30])=[O:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:17][CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66577987Ethyl 4-[4-(benzyloxy)phenyl]-2-(methylsulfonyl)butanoate

생성물 1

HCID 56951003(+/-)-Ethyl 4-[4-(benzyloxy)phenyl]-2-methyl-2-(methylsulfonyl)butanoate수율 91%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Cesium carbonate (9.30 g, 28.5 mmol) was added to ethyl 4-[4-(benzyloxy)phenyl]-2-(methylsulfonyl)butanoate (8.86 g, 23.5 mmol) in DMF (100 mL) and stirred for 30 minutes. Iodomethane was added to the reaction followed by stirring overnight at room temperature. The reaction mixture was poured into 1N aqueous HCl (100 mL) and extracted with EtOAc (3×100 mL). The combined organics were washed with saturated aqueous sodium thiosulfate (100 mL) then dried (MgSO4), filtered and concentrated in vacuo to afford a crude solid. The crude product was purified via silica gel chromatography using an eluant of ethyl acetate in heptane (10-100%) to afford the title compound as a white solid (8.35 g, 90.9%). LC-MS m/z 391.2 (M+1).

후처리

  1. stirringby stirring overnight at room temperature
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organics were washed with saturated aqueous sodium thiosulfate (100 mL)
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a crude solid
  8. customThe crude product was purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-ae2ebe9007594ae39d0c62eb5b266e55
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853258B2

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