Triphenylphosphine → (4R)-4,5-Dihydro-2-(3-iodophenyl)-4-phenyloxazole

HRID 2395365Notes

Reaction equation

HRID 2395365 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][OH:10])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([C:5]2[O:10][CH2:9][C@@H:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:7]=2)[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18665555HCID 18665555, compound

Product 1

HCID 18665564(4R)-4,5-Dihydro-2-(3-iodophenyl)-4-phenyloxazoleYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (+)-2-(3-iodobenzamido)-2(R)-phenylethan-1-ol (14.70 g, 40 mmol) and triphenylphosphine (13.64 g, 52 mmol) in dry tetrahydrofuran (350 ml) was added dropwise a solution of diethyl azodicarboxylate (10.52 g, 52 mmol) in dry tetrahydrofuran (15 ml). The reaction mixture was stirred for 18 h and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:8) to afford (+)-4,5-dihydro-2-(3-iodophenyl)-4(R)-phenyloxazole (7.81 g, 56%) as a liquid.

Workup

  1. customvolatiles removed by evaporation
  2. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:8)

Sources & evidence

ORD record
ord-6e63c50295a8422ab16f434441417cf5
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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