Triphenylphosphine → HCID 59899148, compound

HRID 2227264Notes

Reaction equation

HRID 2227264 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:27])[C@H:15]([CH2:19][CH2:20][C:21]1([CH3:26])[O:25][CH2:24][CH2:23][O:22]1)[CH2:16][CH:17]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:28]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@H:15]([CH2:19][CH2:20][C:21]1([CH3:26])[O:25][CH2:24][CH2:23][O:22]1)[CH2:16][CH:17]=[O:28])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 22086396HCID 22086396, compound

Product 1

HCID 59899148HCID 59899148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-10 (16.0 g, 42.8 mmol) and Sudan III dye (10 mg) in dichloromethane (500 mL) at −78° C. was bubble ozone until the color of the dye was discharged (45 min.), after which time the solution was purged with argon for 0.5 h. Triphenylphosphine (16.9 g, 64.3 mmol) was added and the solution was allowed to warm to ambient temperature for 3 h. The reaction mixture was concentrated at reduced pressure and the resulting oil was purified by flash column chromatography (silica gel, 10 to 20% ethyl acetate/dichloromethane) to give 1-11 as an oil which crystallized on standing.

Workup

  1. custom(45 min.)
  2. customafter which time the solution was purged with argon for 0.5 h
  3. concentrationThe reaction mixture was concentrated at reduced pressure
  4. customthe resulting oil was purified by flash column chromatography (silica gel, 10 to 20% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-38e9523518d84447ac0f7c1a52dc05e2
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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