HCID 19005115, compound → HCID 19005118, compound

HRID 2225918Notes

Reaction equation

HRID 2225918 reaction equation
O=C1[CH:6]([C:7](=[O:17])[C:8]([F:16])([F:15])[CH2:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5][CH2:4][O:3]1>Cl.C(O)(=O)C>[OH:3][CH2:4][CH2:5][CH2:6][C:7](=[O:17])[C:8]([F:16])([F:15])[CH2:9][CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 1

HCID 19005115HCID 19005115, compound

Product 1

HCID 19005118HCID 19005118, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

A 10 mL one neck round bottom flask, fitted with argon inlet, magnetic stirrer, and reflux condenser was charged with 1.0 mL glacial acetic acid, 4 drops of concentrated HCl and 200 mg(0.81 mM) of 2,3,4,5-tetrahydro-2-oxo-3-(5,5-dimethyl-2,2-difluoro-1-oxohexyl)furan. The reaction mixture was heated at 110 C. overnight under a blanket of argon. The reaction was extracted with ethyl ether, and the ether was cross washed with water, dried (anhydrous MgSO4), and solvent removed under reduced pressure. The residue was chromatographed on a 10×60 mm silica gel column using a 9:1 hexane:ethyl acetate mixture to give a clear oil. nmr(CDCl3) -L 0.95(s,9H), 1.45(t,2H), 2.00(m,6H), 3.12(bs,1H), 4.15(m,1H)

Workup

  1. temperaturereflux condenser
  2. temperatureThe reaction mixture was heated at 110 C
  3. customovernight
  4. extractionThe reaction was extracted with ethyl ether
  5. washthe ether was cross washed with water
  6. dry with materialdried (anhydrous MgSO4), and solvent
  7. customremoved under reduced pressure
  8. customThe residue was chromatographed on a 10×60 mm silica gel column
  9. customethyl acetate mixture to give a clear oil

Sources & evidence

ORD record
ord-7d17f65273b54cba80e4a3ed0a29fb24
Source dataset
uspto-grants-1994_09
Patent number
US05344952

Reaction notes

Loading…