Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (6,6-Dimethyl-1,4-dioxan-2-yl)methanol

HRID 1623391노트

반응식

HRID 1623391 반응식
[CH3:1][C:2]([OH:10])([CH3:9])[CH2:3][O:4][CH2:5][CH:6]1[CH2:8][O:7]1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:9])[O:10][CH:6]([CH2:8][OH:7])[CH2:5][O:4][CH2:3]1

참가 물질

5

반응물 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 86650637HCID 86650637, 화합물

생성물 1

HCID 66937181(6,6-Dimethyl-1,4-dioxan-2-yl)methanol수율 64.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-methyl-1-(oxiran-2-ylmethoxy)propan-2-ol (620 mg, 4.24 mmol) and 10-CSA (300 mg, 1.29 mmol) were dissolved in DCM (30 mL) and stirred at ambient temperature for 24 hr. Saturated NaHCO3 solution was added and the two layers were separated. The aqueous phase was extracted four times with DCM. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:2) to give the desired product as a colorless oil (400 mg, 64%). Some starting material was recovered. 1H NMR (400 MHz, CDCl3) δ ppm 3.90-3.96 (1H, m), 3.76 (1H, dd, J=11.2, 2.8 Hz), 3.56 (1H, dd, J=11.6, 4.0 Hz), 3.46-3.50 (2H, m), 3.29 (1H, t, J=11.2 Hz), 3.24 (1H, dd, J=11.6, 1.2 Hz), 2.69 (1H, br s), 1.35 (3H, s), 1.13 (3H, s).

후처리

  1. customthe two layers were separated
  2. extractionThe aqueous phase was extracted four times with DCM
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:2)

출처 및 근거

ORD 기록
ord-c46d8cc8ad6b4bcba8d39e9152eeeac5
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778951B2

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