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

HRID 714260Notes

Reaction equation

HRID 714260 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.CC(C)=[O:19].OS(O)(=O)=O.O=[Cr](=O)=O.C(Cl)Cl>CC(C)=O>[C:1]1([C:7]2([CH2:13][CH2:14][C:15]([OH:19])=[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

5

Reactant 3

HCID 6344DichloromethaneHCID 666854903-(2-phenyltetrahydro-2H-pyran-2-yl)propan-1-olHCID 131709961Jones' reagent

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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 Jones 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-8444c9f75e3341ceba007a62fba1f5ea
Source dataset
uspto-grants-2015_11
Patent number
US09187437B2

Reaction notes

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