HCID 19005115, compound → HCID 19005118, compound

HRID 1762783Notes

Reaction equation

HRID 1762783 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)--α0.95(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-d4b9516a6e524e438aa0e9e52fcc9f95
Source dataset
uspto-grants-1989_05
Patent number
US04835099

Reaction notes

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