4-Toluenesulfonyl chloride → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

HRID 85118

반응식

HRID 85118 반응식
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:8][CH2:7][CH:5]2[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 7528SolketalHCID 8471Triethylamine

생성물 1

HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

(2,2-Dimethyl-1,3-dioxolan-4-yl)methanol (33; 7.56 mmol, 1.0 g) was taken up in 20 mL of dichloromethane. Triethylamine (26.46 mmol, 3.687 mL) was then added, followed by p-toluensulfonyl chloride (15.12 mmol, 2.88 g) and catalytic amount of 4-dimethylamino pyridine. The reaction was allowed to stir at room temperature for 18 h. The crude reaction mixture was diluted with dichloromethane, washed successively with saturated aqueous sodium bicarbonate solution, water, dried (Na2SO4) and concentrated under reduced pressure. The resulting residue 34 was used for the next step without further purification (89% crude yield).

후처리

  1. customThe crude reaction mixture
  2. washwashed successively with saturated aqueous sodium bicarbonate solution, water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue 34 was used for the next step without further purification (89% crude yield)

출처 및 근거

ORD 기록
ord-ac5e6c1e7fdd4b0881b08a7d39fef9a6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846947B2

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