HCID 19005115, compound → HCID 19005118, compound

HRID 1088204Notes

Reaction equation

HRID 1088204 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

Conditions

Temperature
110 °C

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-di-methyl-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 α-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. extractionThe reaction was extracted with ethyl ether
  3. washthe ether was cross washed with water
  4. dry with materialdried (anhydrous MgSO4), and solvent
  5. customremoved under reduced pressure
  6. customThe residue was chromatographed on a 10×60 mm silica gel column
  7. customethyl acetate mixture to give a clear oil

Sources & evidence

ORD record
ord-e62108581e284e258345a717eeff41f7
Source dataset
uspto-grants-1990_10
Patent number
US04962024

Reaction notes

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