Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 1-(Hydroxymethyl)cyclopropyl benzoate

HRID 1517906Notes

Reaction equation

HRID 1517906 reaction equation
[C:1]([O:9][C:10]1([CH2:13][O:14]C2CCCCO2)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[C:1]([O:9][C:10]1([CH2:13][OH:14])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 666699701-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl benzoate

Product 1

HCID 666698541-(Hydroxymethyl)cyclopropyl benzoateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl benzoate (2 g, 7.2 mmol) in 30 mL of MeOH was added PPTS (2.7 g, 10.8 mmol, Aldrich) at rt. The reaction mixture was stirred at rt overnight, then concentrated and purified by a silica gel column chromatography (4:1 (v/v) petroleum ether/EtOAc) to afford the title compound as colorless oil (1.2 g, 87%).

Workup

  1. concentrationconcentrated
  2. custompurified by a silica gel column chromatography (4:1 (v/v) petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-a7ddf63b30614fc89fc2ea48da70d0b8
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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