HCID 57554681, compound → HCID 57554643, compound

HRID 1511896Notes

Reaction equation

HRID 1511896 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:19][CH2:18][CH:17]([OH:20])[CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[O:19][CH2:18][C:17](=[O:20])[CH2:16]2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 57554681HCID 57554681, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57554643HCID 57554643, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-octylphenyl)tetrahydrofuran-3-ol (1 g, 3.62 mmol) was dissolved in dichloromethane (36.2 ml) in a sealed vial. PCC (3.12 g, 14.47 mmol) (Aldrich) was added and the reaction stirred for about 16 h. The methylene chloride was evaporated and the residue stirred with ethyl acetate. The ethyl acetate was filtered through a pad of silica gel (approx. 50 mL silica) and product eluted with ethyl acetate. This removed most of the brown color. Concentrate and then chromatograph on a 40 g redi-sep column with 20-50% ethyl acetate in heptane. Remove solvent under reduced pressure to provide 5-(4-octylphenyl)dihydrofuran-3(2H)-one (0.839 g, 3.06 mmol, 85% yield) as a colorless oil: LC/MS (method A) Rt=4.14 min.; MS m/z: 275.25 (M+H)+.

Workup

  1. customThe methylene chloride was evaporated
  2. stirringthe residue stirred with ethyl acetate
  3. filtrationThe ethyl acetate was filtered through a pad of silica gel (approx. 50 mL silica) and product
  4. washeluted with ethyl acetate
  5. customThis removed most of the brown color
  6. concentrationConcentrate

Sources & evidence

ORD record
ord-df49150019034fd3bddda103f3f43727
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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