4-Toluenesulfonyl chloride → 3-Methoxypropyl 4-methylbenzenesulfonate

HRID 536751Notes

Reaction equation

HRID 536751 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][OH:6].[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][CH2:4][CH2:3][O:2][CH3:1])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 741163-Methoxy-1-propanol

Product 1

HCID 135229883-Methoxypropyl 4-methylbenzenesulfonateYield 76.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxypropan-1-ol (15.9 mL, 166 mmol) in CH2Cl2 (75 mL) and pyridine (50 mL) was added 4-(dimethylamino)pyridine (1.0 g, 8.3 mmol) followed by p-toluenesulfonyl chloride (31.7 g, 166 mmol). The mixture was allowed to stir at ambient temperature for 72 hours then was quenched with 5% aqueous HCl (20 mL), extracted with CH2Cl2 (3×10 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 (31 g, 127 mmol, 76% yield). MS (DCI/NH3) m/z 262 (M+NH4)+.

Workup

  1. customthen was quenched with 5% aqueous HCl (20 mL)
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography (SiO2, 75% hexanes in EtOAc)

Sources & evidence

ORD record
ord-f73933de0356478495dc2879e9f408fe
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

Loading…