m-Chloroperbenzoic acid → (1R,2R,3S,5S)-3-(Hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol
Reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:7]([OH:8])[CH:6]=[CH:5][CH2:4]1.ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)Cl>[OH:1][CH2:2][C@@H:3]1[CH2:4][C@H:5]2[C@H:6]([O:17]2)[C@@H:7]1[OH:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(1S,5S)-5-(Hydroxymethyl)cyclopent-2-en-1-ol (3.19 g, 27.9 mmol) was dissolved in DCM (143 mL) and the solution was cooled to 0° C. 3-Chloroperbenzoic acid (7.52 g, 33.5 mmol) was added and the mixture was stirred at rt for 4 h. TLC indicated complete conversion. Silica gel (20 g) was added, the mixture was concentrated to dryness and was purified via silica gel chromatography eluting with a gradient of 0 to 100% EtOAc in DCM to afford the title compound (2.75 g, 76%). LC/MS: Rt=0.37 min, ES+ 131 (AA standard).
Workup
- additionSilica gel (20 g) was added
- concentrationthe mixture was concentrated to dryness
- customwas purified via silica gel chromatography
- washeluting with a gradient of 0 to 100% EtOAc in DCM
Sources & evidence
- ORD record
- ord-19b82621f3234b74804b733902e7893c
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207177B2
Reaction notes
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