Hydrochloric Acid → HCID 18467891, compound

HRID 2229480Notes

Reaction equation

HRID 2229480 reaction equation
C[O:2][C:3]([C:5]1([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:9]([Si](C)(C)C)[CH2:8][CH2:7][O:6]1)=[O:4].CC(C)([O-])C.[K+].Cl>CS(C)=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:5]2([C:3]([OH:4])=[O:2])[CH2:9][CH2:8][CH2:7][O:6]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18467852HCID 18467852, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18467891HCID 18467891, compoundYield 123.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl-2-(4-fluorophenyl)-3-trimethylsilyl-2-tetrahydrofuroate (16 mg, 0.0541 mmol) in DMSO (0.5 ml) was added potassium t-butoxide (30 mg, 0.270 mmol). The resulting mixture was heated at 60° C. overnight. TLC showed reaction was complete. The reaction mixture was poured into HCl (1N) and extracted with ethyl acetate. The combined organic layer was dried over MgSO4 and concentrated. The residue was purified by preparative TLC eluting with methylene chloride/methanol/acetic acid=95:5:0.5 to give 2-(4-fluorophenyl)-2-tetrahydrofuroic acid (14 mg).

Workup

  1. customreaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC
  6. washeluting with methylene chloride/methanol/acetic acid=95:5:0.5

Sources & evidence

ORD record
ord-a82c5df0458b4b6bb1fb7aa8a8da9245
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

Loading…