Dimethyl Sulfoxide → 6-Benzhydryl-dihydropyran-3-one

HRID 1897881Notes

Reaction equation

HRID 1897881 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]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11608697Trans-6-benzhydryl-tetrahydropyran-3-ol

Product 1

HCID 666316726-Benzhydryl-dihydropyran-3-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

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

  1. additionwas added next
  2. customto come to room temperature for over a period of 30 minutes
  3. washwashed with sat. aqueous NaHCO3, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customRemoval of the solvent and purification by flash chromatography (SiO2, Hexane/Ethyl Acetate 8.5:1.5)

Sources & evidence

ORD record
ord-2ec7bbc4e9154bc383f07359519372be
Source dataset
uspto-grants-2013_08
Patent number
US08519159B2

Reaction notes

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