Triphenylphosphine → 2-(3-benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole

HRID 2395376Notes

Reaction equation

HRID 2395376 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[C:12]([NH:14][C@H:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12]2[O:17][CH2:16][C@@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:24]=[CH:25][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 18665551HCID 18665551, compound

Product 1

HCID 186655522-(3-benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazoleYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-(3-benzyloxybenzamido)-2(R)-phenylethan-1-ol (29 g, 83 mmol) and triphenylphosphine (28.4 g, 108 mmol) in dry tetrahydrofuran (200 ml) was added dropwise a solution of diisopropyl azodicarboxylate (19.6 ml, 108 mmol) in dry tetrahydrofuran (30 ml). The reaction mixture was stirred for 4 hours and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:9) to afford 2-(3-benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole (23.5 g, 85%) as pale yellow solids.

Workup

  1. customvolatiles removed by evaporation
  2. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:9)

Sources & evidence

ORD record
ord-967c0b1674b04201bce01c3d530eea3e
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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