Triphenylphosphine → HCID 55283830, compound

HRID 560566Notes

Reaction equation

HRID 560566 reaction equation
[N:1]([CH2:4][C:5]1[O:6][C:7]([CH:10]([F:12])[F:11])=[CH:8][CH:9]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[F:11][CH:10]([F:12])[C:7]1[O:6][C:5]([CH2:4][NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 866452892-(Azidomethyl)-5-(difluoromethyl)furan

Product 1

HCID 55283830HCID 55283830, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(azidomethyl)-5-(difluoromethyl)furan (0.50 g, 2.92 mmol) in a mixture of tetrahydrofuran (10 mL) and water (1 mL) was added triphenylphosphine (1.15 g, 4.39 mmol). The reaction mixture was stirred at ambient temperature for 18 hours. The solvent was removed in vacuo and the residue was purified on strong cation exchange column to afford (5-(difluoromethyl)furan-2-yl)methanamine as a yellow oil in 70% yield (0.30 g): MS (ES+) m/z 3148.2 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified on strong cation exchange column

Sources & evidence

ORD record
ord-b9762b1229464556805a9b28919527cb
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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