Triphenylphosphine → HCID 59749427, compound

HRID 747224Notes

Reaction equation

HRID 747224 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[C:12]([F:17])[CH:11]=2)[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.O>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH2:6][CH:5]([CH2:4][NH2:1])[O:9][N:8]=2)=[CH:11][C:12]=1[F:17]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 17954492HCID 17954492, compound

Product 1

HCID 59749427HCID 59749427, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

5-(Azidomethyl)-3-(4-bromo-3-fluorophenyl)-4,5-dihydroisoxazole (8.046 g, 26.9 mmol) was dissolved in a mixture of acetonitrile (40 ml) and water (4 ml). Triphenylphosphine (8.48 g, 32.3 mmol) was added and the reaction mixture stirred at room temperature for 48 hours. The reaction mixture was then poured onto a silica gel chromatography column (400 ml). The product was eluted with 10% to 20% water/acetonitrile, then freeze dried to yield 2.67 g of the desired compound.

Workup

  1. additionThe reaction mixture was then poured onto a silica gel chromatography column (400 ml)
  2. washThe product was eluted with 10% to 20% water/acetonitrile
  3. customfreeze dried

Sources & evidence

ORD record
ord-1ccebf78678c452992b566a0a4ba2baf
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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