2,3,4,5-Tetrahydro-1-benzoxepin-5-one → 2,3,4,5-Tetrahydro-1-benzoxepin-5-ol

HRID 1613606Notes

Reaction equation

HRID 1613606 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[OH:12][CH:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:1][CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 3155752,3,4,5-Tetrahydro-1-benzoxepin-5-oneHCID 4311764Sodium borohydride

Product 1

HCID 3155762,3,4,5-Tetrahydro-1-benzoxepin-5-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

121.9 g (0.752 mole) of 2,3-dihydro-1-benzoxepin-5(4H)-one are dissolved in 1,400 ml of methanol and, while stirring vigorously, 18.5 g (0.489 mole) of sodium borohydride are introduced in portions so that the temperature remains below 20° C. The mixture is subsequently stirred for 2 hours, most of the solvent is distilled off in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed with water, 1N potassium bisulfate solution, water and saturated sodium chloride solution and dried over sodium sulfate. The mixture is filtered, and the solvent is evaporated off in vacuo. The oil crystallizes after some time.

Workup

  1. customremains below 20° C
  2. stirringThe mixture is subsequently stirred for 2 hours, most of the solvent
  3. distillationis distilled off in vacuo
  4. washThe organic phase is washed with water, 1N potassium bisulfate solution, water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationThe mixture is filtered
  7. customthe solvent is evaporated off in vacuo
  8. customThe oil crystallizes after some time

Sources & evidence

ORD record
ord-1b27c75db8184c8fba6ba14389466d19
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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