Hydrogen Peroxide → HCID 86690110, compound

HRID 520401Notes

Reaction equation

HRID 520401 reaction equation
[CH3:1][C:2]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:7][CH2:6][CH:5]=[CH:4][O:3]1.B.C1C[O:22]CC1.C([O-])(=O)C.[Na+].OO>C1COCC1.O.CCOC(C)=O>[OH:22][CH:5]1[CH2:4][O:3][C:2]([CH3:1])([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 517045Sodium AcetateHCID 2723981Borane;tetrahydrofuranHCID 86690111HCID 86690111, compound

Product 1

HCID 86690110HCID 86690110, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2-methyl-3,4-dihydro-2H-pyran-2-carboxylate (1.0 g, 3.44 mmol) in THF (10 mL) was added BH3.THF (2.07 mL, 2.07 mmol) dropwise in an ice/acetone bath in 10 min. The reaction mixture was stirred in the bath for 4 h. The reaction mixture was quenched by the addition of a solution of sodium acetate (0.283 g, 3.44 mmol) in water (3 mL). After being stirred for 10 min, H2O2 (0.3 mL, 4.89 mmol) was added. The reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc and washed with sat. NH4Cl, brine, and dried (MgSO4). The solvent was removed in vacuum to afford benzyl 5-hydroxy-2-methyltetrahydro-2H-pyran-2-carboxylate.

Workup

  1. stirringAfter being stirred for 10 min
  2. stirringThe reaction mixture was stirred at rt for 2 h
  3. washwashed with sat. NH4Cl, brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-0d6cab69d3544b46a7ced39deff84656
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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