m-Chloroperbenzoic acid → HCID 58944659, compound

HRID 222193Notes

Reaction equation

HRID 222193 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@:7]([CH3:9])([OH:8])[CH:6]=[CH:5][CH2:4]1.C(=O)(O)[O-:11].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[OH:1][CH2:2][C@@H:3]1[CH2:4][C@H:5]2[C@H:6]([O:11]2)[C@:7]1([CH3:9])[OH:8]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 58944597(1S,2S)-2-Hydroxy-2-methyl-3-cyclopentene-1-methanol

Product 1

HCID 58944659HCID 58944659, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (1S,5S)-5-(hydroxymethyl)-1-methylcyclopent-2-en-1-ol (0.181 g, 0.00141 mol) in DCM (18.0 mL) was added sodium bicarbonate (237 mg, 2.82 mmol) and the mixture was cooled to 0° C. To this mixture was added 3-chloroperbenzoic acid (380. mg, 1.69 mmol) and the reaction was stirred at rt for 4 h. The solvent was removed in vacuo and silica gel chromatography eluting with a gradient of 0 to 100% EtOAc in DCM afforded the title compound (200 mg, 98%). LC/MS: Rt=0.52 min, ES+ 145 (AA standard).

Workup

  1. customThe solvent was removed in vacuo and silica gel chromatography
  2. washeluting with a gradient of 0 to 100% EtOAc in DCM

Sources & evidence

ORD record
ord-0c0968ed851b4fcfa43cc3b18f3ce30a
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

Loading…