4-Toluenesulfonyl chloride → 3-Methoxypropyl 4-methylbenzenesulfonate

HRID 2064505Notes

Reaction equation

HRID 2064505 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(C1C=CN=CC=1)C>[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 DMAP (1.0 g, 8.32 mmol), followed by p-toluenesulfonyl chloride (31.7 g, 166 mmol). This mixture was allowed to stir at ambient temperature for 72 hours, then was quenched with 5% aqueous HCl (30 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 (31 g, 127 mmol, 76% yield). MS (DCI/NH3) m/z 262 (M+NH4).

Workup

  1. customwas quenched with 5% aqueous HCl (30 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography (SiO2, eluted with 75% hexanes in EtOAc)

Sources & evidence

ORD record
ord-ff660f6ef0b542b58f7d8a06b27e72cc
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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