Triphenylphosphine → HCID 18665554, compound

HRID 2395373Notes

Reaction equation

HRID 2395373 reaction equation
[Br: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>[Br: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 18665553HCID 18665553, compound

Product 1

HCID 18665554HCID 18665554, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a mixture of 2-(3-bromobenzamido)-2(R)-phenylethan-1-ol (18 g, 56 mmol) and triphenylphosphine (19.2 g, 73 mmol)) in dry tetrahydrofuran (350 ml) cooled to -60° C. was added dropwise diethyl azodicarboxylate (12 ml, 73 mmol). The reaction mixture was allowed to warm to ambient temperature, stirred for 18 h and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:7) to afford 2-(3-bromophenyl)-4,5-dihydro-4(R)-phenyloxazole (10.9 g, 65%) as a pink liquid.

Workup

  1. temperatureto warm to ambient temperature
  2. customvolatiles removed by evaporation
  3. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:7)

Sources & evidence

ORD record
ord-3b15be9f87664218bce4c44dfb65d73c
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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