Triphenylphosphine → HCID 69005928, compound

HRID 1963745Notes

Reaction equation

HRID 1963745 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.[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 11776TriphenylphosphineHCID 67749Trifluoromethanesulfonic anhydrideHCID 5462222PotassiumHCID 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 carbonated (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-345e745892e640ae937ccb76b8c9d49b
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Reaction notes

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