Tetrahydro-4H-pyran-4-one → 4-[4-(Benzyloxy)phenyl]oxan-4-ol

HRID 51089Notes

Reaction equation

HRID 51089 reaction equation
[Mg].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1>C1COCC1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:20]2([OH:23])[CH2:21][CH2:22][O:17][CH2:18][CH2:19]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5462224Magnesium

Product 1

HCID 227373514-[4-(Benzyloxy)phenyl]oxan-4-olYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a 100 ml round-bottomed flask was placed magnesium turnings (1.85 g, 76.1 mmol), which was stirred under vacuum without solvent overnight. To it were slowly added anhydrous THF 40 ml and 4-benzyloxy bromobenzene (10 g, 38 mmol) over 15 min with occasional heating by a heat gun to keep the Grignard reagent formation going. After the addition was complete, the resulting gray slurry was stirred for 1 hr at 60° C. To it was added tetrahydro-4H-pyran-4-one (3.5 ml, 38 mmol) upon cooling in an ice-water bath. After stirring for 30 min, the solvent was removed under reduced pressure and diluted with AcOEt and sat. NH4Cl aq. The organic phase was separated, concentrated, and chromatographed on silica gel eluting with 40% AcOEt/hexanes to give 4-(4-benzyloxyphenyl)tetrahydro-2H-pyran-4-ol 5.95 g (55%).

Workup

  1. customIn a 100 ml round-bottomed flask was placed
  2. customover 15 min
  3. temperaturewith occasional heating by a heat gun
  4. additionAfter the addition
  5. temperatureupon cooling in an ice-water bath
  6. stirringAfter stirring for 30 min
  7. customthe solvent was removed under reduced pressure
  8. additiondiluted with AcOEt and sat. NH4Cl aq. The organic phase
  9. customwas separated
  10. concentrationconcentrated
  11. customchromatographed on silica gel eluting with 40% AcOEt/hexanes

Sources & evidence

ORD record
ord-389e413d8f4d474694d1d973c75b52f1
Source dataset
uspto-grants-2004_03
Patent number
US06713508B2

Reaction notes

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