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

HRID 1963942노트

반응식

HRID 1963942 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-0315e60c1da141729a4cfd8fd3b7c15c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415381B2

반응 노트

불러오는 중…