Dimethyl Sulfoxide → 6-((benzyloxy)methyl)dihydro-2H-pyran-3(4H)-one
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][CH2:19][CH:20]1[O:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.[NH4+].[Cl-]>ClCCl>[CH2:11]([O:18][CH2:19][CH:20]1[O:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
DMSO (1.15 mL, 16.2 mmol) was added to a stirred solution of oxalyl chloride (1 mL, 10.8 mmol) in dichloromethane (60 mL) at −78° C. After 10 minutes, a dichloromethane solution of 6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol (14) (1.20 g, 5.40 mmol) was added. Stirring was continued for one hour then triethylamine (3.8 mL, 27 mmol) was added and slowly warmed to 0° C. The reaction was poured into saturated NH4Cl solution and the organic phase was washed with brine and dried (NaSO4). The residue was purified over silica gel using EtOAc and hexanes to give 6-(benzyloxymethyl)dihydro-2H-pyran-3(4H)-one (15).
Workup
- waitwas continued for one hour
- washthe organic phase was washed with brine
- dry with materialdried (NaSO4)
- customThe residue was purified over silica gel
Sources & evidence
- ORD record
- ord-3663cbdaaeb047ac91dd5d57d64ae722
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754071B2
Reaction notes
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