Hydrogen Peroxide → 3-(2-phenyltetrahydro-2H-pyran-2-yl)propan-1-ol

HRID 714259Notes

Reaction equation

HRID 714259 reaction equation
[CH2:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][O:5]1)[CH:2]=[CH2:3].[OH2:16].[OH-].[Na+].OO>C1COCC1>[C:10]1([C:4]2([CH2:1][CH2:2][CH2:3][OH:16])[CH2:9][CH2:8][CH2:7][CH2:6][O:5]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 666850742-allyl-2-phenyltetrahydro-2H-pyran

Product 1

HCID 666854903-(2-phenyltetrahydro-2H-pyran-2-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-allyl-2-phenyltetrahydro-2H-pyran (700 mg, 3.46 mmol) in THF (7 mL) at 0° C. was added 1M borane tetrahydrofuran complex (1.730 mL, 1.730 mmol) dropwise, and the mixture was stirred overnight at room temperature. After cooling to 0° C., water (0.07 ml) was added to destroy the excess borane. After stirring for 10 mins, 3M NaOH (0.42 mL, 1.260 mmol) was added and stirred for 10 mins. Then 30% H2O2 (0.42 mL, 4.11 mmol) was added and the cooling bath was removed. It was refluxed for 1.5 hrs and cooled to room temperature. It was extracted with EtOAc (2×), and the combined extracts were washed with brine, dried over Na2SO4 and evaporated to give 3-(2-phenyltetrahydro-2H-pyran-2-yl)propan-1-ol as oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.11-7.44 (5 H, m), 3.66-3.81 (2 H, m), 3.48-3.59 (2 H, m), 2.22-2.37 (2 H, m), 1.35-1.89 (8 H, m).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customto destroy the excess borane
  3. stirringAfter stirring for 10 mins
  4. stirringstirred for 10 mins
  5. customthe cooling bath was removed
  6. temperatureIt was refluxed for 1.5 hrs
  7. temperaturecooled to room temperature
  8. extractionIt was extracted with EtOAc (2×)
  9. washthe combined extracts were washed with brine
  10. dry with materialdried over Na2SO4
  11. customevaporated

Sources & evidence

ORD record
ord-f3e3c46868664d2195d68d429fefc803
Source dataset
uspto-grants-2015_11
Patent number
US09187437B2

Reaction notes

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