4-Toluenesulfonyl chloride → Cyclopentylmethyl 4-methylbenzene-1-sulfonate

HRID 536754Notes

Reaction equation

HRID 536754 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>CN(C)C1C=CN=CC=1.ClCCl.N1C=CC=CC=1.Cl>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

7

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 77195Cyclopentanemethanol

Product 1

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonateYield 76%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of cyclopentylmethanol (8.7 g, 87 mmol) and 4-(dimethylamino)pyridine (0.5 g, 4.3 mmol) in dichloromethane (30 mL) and pyridine (30 mL) was added 4-methylbenzene-1-sulfonyl chloride (16.6 g, 87 mmol). The mixture was stirred at ambient temperature for 20 hours then diluted with 2 N aqueous HCl and extracted with dichloromethane (3×10 mL). The combined organic extracts were dried with NaSO4, concentrated and the filtered thru a silica plug using hexanes:EtOAc (3:1) to afford the title compound (16.5 g, 64.9 mmol, 76% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.12-1.27 (m, 2H), 1.47-1.61 (m, 4H), 1.64-1.78 (m, 2H), 2.12-2.30 (m, 1H), 2.45 (s, 3H), 3.90 (d, J=7.1 Hz, 2H), 7.32-7.36 (m, 2H), 7.76-7.81 (m, 2H); MS (DCI/NH3) m/z 272.1 (M+NH4)+.

Workup

  1. extractionextracted with dichloromethane (3×10 mL)
  2. dry with materialThe combined organic extracts were dried with NaSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9214d392f31549a6a2030fa5a084cde2
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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