4-Toluenesulfonyl chloride → 1-(2-Methyl-1,3-dioxolan-2-yl)-1-p-toluenesulfonyloxymethylcyclopropane

HRID 1613556Notes

Reaction equation

HRID 1613556 reaction equation
[OH:1][CH2:2][C:3]1([C:6]2([CH3:11])[O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:11][C:6]1([C:3]2([CH2:2][O:1][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH2:4][CH2:5]2)[O:7][CH2:8][CH2:9][O:10]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22042312[1-(2-Methyl-1,3-dioxolan-2-yl)cyclopropyl]methanol

Product 1

HCID 536511091-(2-Methyl-1,3-dioxolan-2-yl)-1-p-toluenesulfonyloxymethylcyclopropane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred and ice-cooled solution of 3 (5.0 g, 31.6 mmol), N,N-dimethyl-4-aminopyridine (386 mg, 8.16 mmol) and triethylamine (22 mL, 158 mmol) in dichloromethane (25 mL) was added p-toluenesulfonyl chloride (7.23 g, 37.9 mmol) portionwise and the mixture was stirred in a cold room at 4° C. overnight. The mixture was poured into ice water, and the organic layer was separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water and brine, and dried over sodium sulfate. Filtration and concentration gave 16.70 g of crude 4, as a pale yellow oil, which was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred in a cold room at 4° C. overnight
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration
  7. customgave 16.70 g of crude 4
  8. customas a pale yellow oil, which was used in the next step without further purification

Sources & evidence

ORD record
ord-a9cf13ab579f4170aa24ba0d12a63f5b
Source dataset
uspto-grants-1993_03
Patent number
US05194431

Reaction notes

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