Triphenylphosphine → HCID 18665550, compound

HRID 2395390Notes

Reaction equation

HRID 2395390 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][N:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:39]([O:44][CH2:45][CH2:46]O)(=[O:43])[C:40]([CH3:42])=[CH2:41].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:39]([O:44][CH2:45][CH2:46][O:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:9]2[O:10][C@H:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:12][N:13]=2)[C:2]=1[F:1])(=[O:43])[C:40]([CH3:42])=[CH2:41]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 133602-Hydroxyethyl MethacrylateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18665560HCID 18665560, compound

Product 1

HCID 18665550HCID 18665550, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4,5-dihydro-2-(2-fluoro-3-hydroxyphenyl)-5(R)-phenyloxazol e (0.97 g, 3.8 mmol), triphenylphosphine (1.0 g, 4.0 mmol) and 2-hydroxyethyl methacrylate (0.50 ml, 4.0 mmol) in THF (30 ml) was added dropwise a solution of diethyl azodicarboxylate (0.65 ml, 4.0 mmol) in THF (15 ml). After stirring for 1 day, volatiles were removed by evaporation. The residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (2:1) to afford the title compound (1.2 g, 86%) as a pale yellow liquid.

Workup

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

Sources & evidence

ORD record
ord-d1c93465dde44af583b6f45909eb9621
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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