Hydrogen Peroxide → Trans-6-benzhydryl-tetrahydropyran-3-ol
Reaction equation
[CH:1]([CH:14]1[CH2:19][CH2:18][CH:17]=[CH:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:20].[Na+].OO>C1COCC1.C([O-])(O)=O.[Na+]>[CH:1]([C@@H:14]1[O:15][CH2:16][C@@H:17]([OH:20])[CH2:18][CH2:19]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
Into a solution of 0.5M 9-BBN-THF complex (24 ml, 12 mmol) in dry THF (20 ml) was added in a drop wise manner 2-diphenyl-3,4-dihydro-2H-pyran 10 (1 g, 4 mmol) dissolved in dry THF (10 ml). The mixture was kept under stirring at room temperature. After the completion of initial addition reaction, the intermediate reaction mixture was oxidized with 5.3 ml 3N sodium hydroxide and 3 ml of 30% hydrogen peroxide. The reaction was continued at 55° C. for 1 hr to insure the completion of oxidation. After the mixture was diluted with sat. aqueous NaHCO3, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×40 ml). The combined extract was dried over anhydrous Na2SO4. The solvent was removed in vacuo and the crude product was purified by flash chromatography (Hexane/Ethyl Acetate 7:3) to furnish trans-6-diphenyltetrahydropyran-3-ol 11 (1 g, 93.5%) as a liquid.
Workup
- additionAfter the completion of initial addition reaction
- customthe intermediate reaction mixture
- customthe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate (3×40 ml)
- extractionThe combined extract
- dry with materialwas dried over anhydrous Na2SO4
- customThe solvent was removed in vacuo
- customthe crude product was purified by flash chromatography (Hexane/Ethyl Acetate 7:3)
Sources & evidence
- ORD record
- ord-7db7d5bd03bd4c09af36333f285de14c
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08519159B2
Reaction notes
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