Delta-Valerolactone → 2-phenyltetrahydro-2H-pyran-2-ol

HRID 71259

Reaction equation

HRID 71259 reaction equation
[C:1]1(=[O:7])[O:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1([Mg]Br)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[C:8]1([C:1]2([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][O:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 10953Delta-ValerolactoneHCID 178418255HCID 178418255, compound

Product 1

HCID 145879022-phenyltetrahydro-2H-pyran-2-olYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of delta-valerolactone (1.854 mL, 19.98 mmol) in THF (20 mL) was added 1M phenylmagnesium bromide (19.98 mL, 19.98 mmol) dropwise at room temperature (exothermic), and the mixture was stirred at room temperature for 5 hrs. Then the reaction was quenched with saturated NH4Cl and extracted with EtOAc. The extract was washed with brine, and the combined aqueous layers were back extracted with EtOAc once and combined. The extracts were dried over Na2SO4 and evaporated to give an oily residue. It was purified by Combiflash (120 g silica gel) eluting with 4:6 followed by 1:1 EtOAc-hexane to give 1.97 g of 2-phenyltetrahydro-2H-pyran-2-ol as oil. 1H NMR (400 MHz, CCl3D) δ ppm 7.92-8.00 (1H, m), 7.17-7.60 (5H, m), 3.67 (1H, t, J=6.15 Hz), 3.03 (1H, t, J=7.14 Hz), 2.25-2.37 (1H, m), 1.75-1.92 (2H, m), 1.54-1.71 (2H, m), 1.30-1.43 (1H, m).

Workup

  1. customThen the reaction was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. extractionthe combined aqueous layers were back extracted with EtOAc once
  5. dry with materialThe extracts were dried over Na2SO4
  6. customevaporated
  7. customto give an oily residue
  8. customIt was purified by Combiflash (120 g silica gel)
  9. washeluting with 4:6

Sources & evidence

ORD record
ord-dd908e9f867a4df3a1f2e89816967d6f
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Linked notes

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