Dimethyl Sulfoxide → 6-((benzyloxy)methyl)dihydro-2H-pyran-3(4H)-one

HRID 1045405Notes

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]=1

Participants

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 dichlotomethane 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-c1f36ece35b8490a87ba36277688477d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569283B2

Reaction notes

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