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

HRID 625690Notes

Reaction equation

HRID 625690 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, 14.1 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, 14.1 mmol). The mixture is stirred overnight then washed with 1 M 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). LC (METHOD 2): tR=5.67 min; Mass spectrum (ES+): m/z=258 [M+H]+.

Workup

  1. washthen washed with 1 M 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-66313e4cd27a45ae9684abc7670069b3
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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