1-Pentanol → Pentyl toluene-4-sulphonate

HRID 2064489Notes

Reaction equation

HRID 2064489 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[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][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 62761-PentanolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 78195Pentyl toluene-4-sulphonateYield 63.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of pentan-1-ol (9.2 mL, 85 mmol) in CH2Cl2 (70 mL) and pyridine (50 mL) was added DMAP (0.52 g, 4.3 mmol) followed by p-toluenesulfonyl chloride (16.2 g, 85 mmol). This mixture was allowed to stir at ambient temperature for 18 hours then quenched with 5% aqueous HCl (20 mL) and diluted with EtOAc (20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×7 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 75% hexanes in EtOAc) to give the title compound (13.1 g, 53.9 mmol, 63% yield). MS (DCI/NH3) m/z 260 (M+NH4)−.

Workup

  1. customthen quenched with 5% aqueous HCl (20 mL)
  2. additiondiluted with EtOAc (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×7 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, 75% hexanes in EtOAc)

Sources & evidence

ORD record
ord-4f2f16ce98ca41cba7c11df28fae155b
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

Loading…