Trimethyl orthoformate → Tert-butyl 3,3-dimethoxycyclopentanecarboxylate

HRID 1816959노트

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HRID 1816959 반응식
O=[C:2]1C[CH2:5][CH:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.CO[CH:16]([O:19][CH3:20])[O:17][CH3:18]>CC1C=CC(S(O)(=O)=O)=CC=1.O.C(Cl)Cl.CO>[CH3:20][O:19][C:16]1([O:17][CH3:18])[CH2:2][CH2:3][CH:4]([C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[CH2:5]1

참가 물질

5

반응물 2

HCID 9005Trimethyl orthoformateHCID 14009986tert-Butyl 3-oxocyclopentane-1-carboxylate

생성물 1

HCID 58784445Tert-butyl 3,3-dimethoxycyclopentanecarboxylate수율 90.1%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매2회HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution of tert-butyl 3-oxocyclopentanecarboxylate (19.8 g, 107 mmol) in 1:1 DCM/methanol (150 mL) was added trimethylorthoformate (46.8 mL, 428 mmol), followed by TsOH.H2O (˜0.5 g). The reaction mixture was stirred at room temperature for 2 h. Then more TsOH.H2O (˜0.25 g) was added and the reaction mixture was stirred overnight. The reaction mixture was concentrated at room temperature and the resulting residue was dissolved in ether and washed with saturated NaHCO3 solution, then with brine. The ethereal layer was dried over anhydrous MgSO4, filtered, and concentrated. Purification by flash chromatography (silica, 15% ethyl acetate/hexane) gave 22.2 g (90%) of tert-butyl 3,3-dimethoxycyclopentanecarboxylate.

후처리

  1. stirringthe reaction mixture was stirred overnight
  2. concentrationThe reaction mixture was concentrated at room temperature
  3. dissolutionthe resulting residue was dissolved in ether
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialThe ethereal layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (silica, 15% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-54082dc2ff724e2185a44c42f5c845fa
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598243B2

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