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

HRID 85118

Reaction equation

HRID 85118 reaction equation
[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

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 7528SolketalHCID 8471Triethylamine

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(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).

Workup

  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)

Sources & evidence

ORD record
ord-ac5e6c1e7fdd4b0881b08a7d39fef9a6
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Linked notes

Loading…