Diazomethane → rac-methyl (3R,5S)-5-hydroxyoxane-3-carboxylate
Reaction equation
[N+](=[CH2:3])=[N-].[OH:4][C@H:5]1[CH2:10][O:9][CH2:8][C@@H:7]([C:11]([OH:13])=[O:12])[CH2:6]1>C(OCC)C.CO>[OH:4][C@H:5]1[CH2:10][O:9][CH2:8][C@@H:7]([C:11]([O:13][CH3:3])=[O:12])[CH2:6]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of diazomethane in diethyl ether (approx. 0.4 M) is added in excess to a solution of 23 mmol of (cis)-5-hydroxytetrahydropyran-3-carboxylic acid in 300 ml of methanol at 0° C. The mixture is stirred at 0° C. for 2 hours and then quenched with magnesium sulphate, filtered and evaporated. The crude title compound is identified by means of the Rf.
Workup
- customquenched with magnesium sulphate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-1e55ef36458c48b4ac63172872a7f8d4
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071651B2
Reaction notes
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