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

HRID 1623391ノート

反応式

HRID 1623391 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c46d8cc8ad6b4bcba8d39e9152eeeac5
出典データセット
uspto-grants-2014_07
特許番号
US08778951B2

反応ノート

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