Triphenylphosphine → 7-(2-Methyl-[1,3]dioxolan-2-yl)-4-(2-oxo-oxazolidine-3-carbonyl)-heptanal

HRID 322072Notes

Reaction equation

HRID 322072 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH:10]([CH2:19][CH2:20][CH:21]=C)[C:11]([N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[O:12])[O:6][CH2:5][CH2:4][O:3]1.[O:23]=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH:10]([C:11]([N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[O:12])[CH2:19][CH2:20][CH:21]=[O:23])[O:3][CH2:4][CH2:5][O:6]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 220088813-(2-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-hex-5-enoyl)-oxazolidin-2-one

Product 1

HCID 220088697-(2-Methyl-[1,3]dioxolan-2-yl)-4-(2-oxo-oxazolidine-3-carbonyl)-heptanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-4 (1.8 g, 5.8 mmol), sudan III (10 mg) and CH2Cl2 (150 mL) at −78° C. under argon was bubbled ozone until the red solution changed to yellow-orange. The solution was purged with argon for 30 minutes. PPh3 (2.26 g, 8.7 mmol) was added followed by the removal of the cooling bath. After 1.5 h, the reaction was concentrated. Flash chromatography (silica, 20%-50% EtOAc/hexanes) gave 2-5 as a yellow solid.

Workup

  1. customThe solution was purged with argon for 30 minutes
  2. customfollowed by the removal of the cooling bath
  3. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-4e1768a051bd4f348b32beff339fd801
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Reaction notes

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