Pyridine → 2-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

HRID 471443Notes

Reaction equation

HRID 471443 reaction equation
[CH3:1][C:2]([OH:7])([CH3:6])[CH2:3][CH2:4][OH:5].N1C=CC=CC=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl>[OH:7][C:2]([CH3:6])([CH3:1])[CH2:3][CH2:4][O:5][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 247470Isopentyldiol

Product 1

HCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-1,3-butanediol (1.5 mL, 14.06 mmol) is suspended in dry dichloromethane (5 mL) and pyridine (1.24 mL, 15.46 mmol) is added followed by 4-toluenesulfonyl chloride (2.68 g, 14.06 mmol). The mixture is stirred overnight then washed with 1M aqueous hydrochloric acid, dried and the solvent removed under vacuum. The residue is purified by flash chromatography (0-30% ethyl acetate in cyclohexane) to give the title compound. (Yield 970 mg).

Workup

  1. washthen washed with 1M aqueous hydrochloric acid
  2. customdried
  3. customthe solvent removed under vacuum
  4. customThe residue is purified by flash chromatography (0-30% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-bb09df4db3c347ce857da955ffe58b1a
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

Loading…