Acetone → 3-(2-phenyltetrahydro-2H-pyran-2-yl)propanoic acid

HRID 71262Notes

Reaction equation

HRID 71262 reaction equation
[C:1]1([C:7]2([CH2:13][CH2:14][CH2:15][OH:16])[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.CC(C)=[O:22]>>[C:1]1([C:7]2([CH2:13][CH2:14][C:15]([OH:22])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 6344DichloromethaneHCID 666854903-(2-phenyltetrahydro-2H-pyran-2-yl)propan-1-ol

Product 1

HCID 666852873-(2-phenyltetrahydro-2H-pyran-2-yl)propanoic acid

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(2-phenyltetrahydro-2H-pyran-2-yl)propan-1-ol (640 mg, 2.91 mmol) in acetone (10 mL) at 0° C. was added 4.15 mL of 0.7 M Jone's reagent, and the mixture was stirred for 30 mins at 0° C. and for 1 hr at room temperature. It was added to CH2Cl2 and washed with water twice. The extract was dried over Na2SO4 and evaporated to give an oily residue. The residue was purified by Combiflash (40 g silica gel) eluting with 4:6 EtOAc-hexane to 3-(2-phenyltetrahydro-2H-pyran-2-yl)propanoic acid (346 mg). LC/MS: m/e 235.21 (M+H)+.

Workup

  1. washwashed with water twice
  2. dry with materialThe extract was dried over Na2SO4
  3. customevaporated
  4. customto give an oily residue
  5. customThe residue was purified by Combiflash (40 g silica gel)
  6. washeluting with 4:6 EtOAc-hexane to 3-(2-phenyltetrahydro-2H-pyran-2-yl)propanoic acid (346 mg)

Sources & evidence

ORD record
ord-74181aba6200419eb8b994ef8d617f6f
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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