Dimethyl Sulfoxide → 6-Benzhydryl-dihydropyran-3-one
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:11]([C@@H:24]1[O:29][CH2:28][C@@H:27]([OH:30])[CH2:26][CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:11]([CH:24]1[O:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
Procedure
Into a solution of DMSO (0.13 g, 1.64 mmol) in methylene chloride (5 ml) at −78° C. was added a solution of oxalyl chloride (0.11 g, 0.82 mmol) in methylene chloride (1 ml) in a dropwise manner. A solution of trans-2-diphenylmethyl-tetrahydropyran-5-ol 11 (0.2 g, 0.75 mmol) in methylene chloride (2 ml) was added next. The reaction was continued for 15 minutes, triethylamine (0.38 g, 3.73 mmol) was next added portion wise and the reaction mixture was allowed to come to room temperature for over a period of 30 minutes. Additional methylene chloride (10 ml) was added, and washed with sat. aqueous NaHCO3, brine, and then dried over anhydrous Na2SO4. Removal of the solvent and purification by flash chromatography (SiO2, Hexane/Ethyl Acetate 8.5:1.5) gave 2-diphenylmethyl-dihydro-pyran-5-one 12 (0.18 g, 91%) as a liquid.
Workup
- customto come to room temperature for over a period of 30 minutes
- washwashed with sat. aqueous NaHCO3, brine
- dry with materialdried over anhydrous Na2SO4
- customRemoval of the solvent and purification by flash chromatography (SiO2, Hexane/Ethyl Acetate 8.5:1.5)
Sources & evidence
- ORD record
- ord-dd5be13434c74061a3fd5db1527d207e
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017791B2
Reaction notes
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