4-Toluenesulfonyl chloride → (2R)-2-(4-Chlorophenyl)-2-cyclopropylethyl 4-methylbenzenesulfonate

HRID 1835031Notes

Reaction equation

HRID 1835031 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH:11]2[CH2:13][CH2:12]2)[CH2:9][OH:10])=[CH:4][CH:3]=1.[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].C(N(CC)CC)C>ClCCl>[CH3:21][C:20]1[CH:22]=[CH:23][C:17]([S:14]([O:10][CH2:9][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:11]2[CH2:13][CH2:12]2)(=[O:16])=[O:15])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 59882239(2R)-2-(4-chlorophenyl)-2-cyclopropylethanol

Product 1

HCID 86584690(2R)-2-(4-Chlorophenyl)-2-cyclopropylethyl 4-methylbenzenesulfonateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-(4-Chlorophenyl)-2-cyclopropylethanol (6.50 g, 33.0 mmol), tosyl chloride (7.86 g, 41.0 mmol) and 6.0 ml of triethylamine (6.0 ml) are dissolved in dichloromethane (150 ml) and allowed to stir for 3 days. The reaction mixture is washed successively with 1 N HCl (100 ml), water (100 ml) and saturated brine solution (100 ml). The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel eluting with ether:hexane (10:90 to 25:75) to afford the title compound as a colorless oil (11.1 g, 96%) which is characterized by 1HNMR, 13CNMR and mass spectral analysis.

Workup

  1. washThe reaction mixture is washed successively with 1 N HCl (100 ml), water (100 ml) and saturated brine solution (100 ml)
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is chromatographed on silica gel eluting with ether:hexane (10:90 to 25:75)

Sources & evidence

ORD record
ord-0224d4d3522649959f539b73fd36c596
Source dataset
uspto-grants-2004_08
Patent number
US06770463B2

Reaction notes

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