Triphenylphosphine → 6-(2-Methyl-[1,3]dioxolan-2-yl)-3-(2-oxo-oxazolidine-3-carbonyl)-hexanal

HRID 1108385Notes

Reaction equation

HRID 1108385 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH:10]([CH2:19][CH:20]=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:22]=[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][CH:20]=[O:22])[O:3][CH2:4][CH2:5][O:6]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 154537583-(2-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-pent-4-enoyl)-oxazolidin-2-one

Product 1

HCID 154537596-(2-Methyl-[1,3]dioxolan-2-yl)-3-(2-oxo-oxazolidine-3-carbonyl)-hexanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-4 (4.0 g, 13.5 mmol), sudan III (10 mg) and CH2Cl2 (350 mL) at -78° C. under argon was bubbled ozone until red solution changed to yellow-orange. The solution was purged with argon for 30 minutes. PPh3 (5.28 g, 20.3 mmol) was added followed by the removal of the cooling bath. After 3.0 h, the reaction was concentrated. Flash chromatography (silica, 20%-50% EtOAc/hexanes) gave 2-5 as a yellow oil.

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-d82e044c259747228b6347c93da52fe7
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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