4-Toluenesulfonyl chloride → Cyclobutylmethyl 4-methylbenzenesulfonate

HRID 2064497Notes

Reaction equation

HRID 2064497 reaction equation
[CH:1]1([CH2:5][OH:6])[CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>C(Cl)Cl.N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:17][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:6][CH2:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 78130Cyclobutylcarbinol

Product 1

HCID 13163931Cyclobutylmethyl 4-methylbenzenesulfonateYield 89%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclobutanemethanol (11.0 mL, 116 mmol) in CH2Cl2 (35 mL) and pyridine (35 mL) was added DMAP (0.71 g, 5.81 mmol) followed by p-toluenesulfonyl chloride (22.1 g, 116 mmol). This mixture was allowed to stir at ambient temperature for 16 hours then was quenched with 5% aqueous HCl (40 mL) and diluted with CH2Cl2 (20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, eluted with 75% hexanes in EtOAc) to give the title compound (24.7 g, 103 mmol, 89% yield). MS (DCI/NH3) m/z 258 (M+NH4)+.

Workup

  1. customthen was quenched with 5% aqueous HCl (40 mL)
  2. additiondiluted with CH2Cl2 (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography (SiO2, eluted with 75% hexanes in EtOAc)

Sources & evidence

ORD record
ord-7d7998cb62d0469da7bd5519b23baef9
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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