Dimethyl Sulfoxide → HCID 57166164, compound

HRID 1492008Notes

Reaction equation

[C:1](Cl)(=[O:5])[C:2](Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][CH2:14][CH:15]1[CH2:19][CH2:18][O:17][CH:16]1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.C(N([CH:32]([CH3:34])[CH3:33])CC)(C)C>C(Cl)Cl>[C:14]1([C:33]2[CH:32]=[CH:34][CH:21]=[CH:20][CH:25]=2)[CH:15]=[CH:16][C:2]([CH2:1][O:5][C@H:19]2[CH2:18][O:17][C@H:16]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[C@@H:15]2[CH2:14][CH2:13][CH:12]=[O:11])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of 0.48 g (0.00383 mole) of oxalyl chloride in 7 ml of methylene chloride is added dropwise a solution of 0.54 g (0.0067 mole) of dimethylsulfoxide in 4 ml of dichloromethane with stirring at -60° C. After stirring the mixture for another 10 min at -70° C., a solution of 0.95 g (0.00244 mole) of (2S,3S,4R)-4-(biphenyl)-4-ylmethoxy)-3-(3-hydroxyprop-1-yl)-2-(3-pyridyl)tetrahydrofuran in 8 ml of dichloromethane is added dropwise over a period of 10 min. The mixture is stirred at -70° C. for 1 h and 2.48 ml (0.014 mole) of diisopropylethyl amine are added at once. The mixture is allowed to warm up to room temperature, washed with water and brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography using methylene chloride-methanol-ammonium hydroxide (300:25:1) as eluent to give (2S,3S,4R)-3-[4-(biphenyl-4-ylmethoxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]propanal as oil.

Workup

stirringAfter stirring the mixture for another 10 min at -70° C.
stirringThe mixture is stirred at -70° C. for 1 h
temperatureto warm up to room temperature
washwashed with water and brine
dry with materialdried (MgSO4)
customevaporated
customThe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-70b0d3f12d64470eb1a457b42d971cfd
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05371096

Reaction notes

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