Potassium Carbonate → HCID 69005928, compound

HRID 30827Notes

Reaction equation

HRID 30827 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[F:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][C:37]=1[C:45]([CH3:51])([CH2:48][CH2:49][OH:50])[CH2:46]O.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[F:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][C:37]=1[C:45]1([CH3:51])[CH2:48][CH2:49][O:50][CH2:46]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 67749Trifluoromethanesulfonic anhydrideHCID 690042812-(2-Fluoro-5-nitrophenyl)-2-methylbutane-1,4-diol

Product 1

HCID 69005928HCID 69005928, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphenylphosphine(2 eq) in dichloromethane at 0° C. under nitrogen was added dropwise triflic anhydride(1 eq). After 15 minutes 2-(2-fluoro-5-nitrophenyl)-2-methylbutane-1,4-diol(1 eq)was added in dichloromethane followed by potassium carbonate(1 eq). The resulting mixture was allowed to warm to room temperature for 5 h. To the mixture was added water and extracted with dichloromethane. The organic layer was washed with brine and dried with sodium sulfate and concentrated. Crude product was purified using flash chromatography (85% Hex:15% EtoAc) on silica to afford 3-(2-fluoro-5-nitrophenyl)-tetrahydro-3-methylfuran.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customCrude product was purified

Sources & evidence

ORD record
ord-68e31c49ce974288bffe3c5f85382c39
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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