4-Toluenesulfonyl chloride → Cyclobutylmethyl 4-methylbenzenesulfonate

HRID 536738

Reaction equation

HRID 536738 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(C)C1C=CN=CC=1>[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 73%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclobutylmethanol (25 g, 290 mmol) in CH2Cl2 (200 mL) and pyridine (100 mL) was added 4-(dimethylamino)pyridine (1.8 g, 14.5 mmol) followed by p-toluenesulfonyl chloride (55.3 g, 290 mmol). The mixture was allowed to stir at ambient temperature for 20 hours then quenched with 5% aqueous HCl (30 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 75% hexanes in EtOAc) afforded the title compound (50.8 g, 211 mmol, 73% yield). MS (DCI/NH3) m/z 258 (M+NH4)+.

Workup

  1. customthen quenched with 5% aqueous HCl (30 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×15 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (SiO2, 75% hexanes in EtOAc)

Sources & evidence

ORD record
ord-53306f91990749859c5bdde3186e8017
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Linked notes

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