Triphenylphosphine → 3-[2-(4-Bromophenyl)ethyl]-1,3-oxazolidine-2,4-dione

HRID 1867534Notes

Reaction equation

HRID 1867534 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:30]1[CH2:34][C:33](=[O:35])[NH:32][C:31]1=[O:36].N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:32]2[C:33](=[O:35])[CH2:34][O:30][C:31]2=[O:36])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 728512-(4-Bromophenyl)ethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 973892,4-Oxazolidinedione

Product 1

HCID 675289483-[2-(4-Bromophenyl)ethyl]-1,3-oxazolidine-2,4-dione

Procedure

The procedure described in Example 2 (step 2.1.) is used; starting from 4 g (19.89 mmol) of 2-(4-bromophenyl)ethanol, 6.3 g (23.87 mmol) of triphenylphosphine, 2.4 g (23.87 mmol) of 1,3-oxazolidine-2,4-dione and 4.8 g (23.87 mmol) of diisopropyl azodicarboxylate, 4.6 g of pure product are obtained in the form of a white solid, after chromatography on silica gel, eluting with dichloromethane.

Workup

  1. customare obtained in the form of a white solid
  2. washafter chromatography on silica gel, eluting with dichloromethane

Sources & evidence

ORD record
ord-c027a185b48c4f0b8ab02f23f882c6bc
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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