Triphenylphosphine → Methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazoline-4-carboxylate

HRID 891055Notes

Reaction equation

O[CH2:2][CH:3]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)=[O:10])[C:4]([O:6][CH3:7])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[F:18][C:17]([F:20])([F:19])[C:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][CH2:2][CH:3]([C:4]([O:6][CH3:7])=[O:5])[N:8]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]-carbonylamino}propanoate (2.57 g, 8.83 mmol) in tetrahydrofuran (30 ml) was added triphenylphosphine (2.55 g, 9.71 mmol). The mixture was cooled to 0° C., and diisopropylazodicarboxylate (1.91 ml, 9.71 mmol) was added slowly. The mixture was stirred at room temperature for 2 days. Solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography, to yield methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazoline-4-carboxylate, a compound of formula (14). C. Preparation of a Compound of Formula (15)

Workup

customSolvent was removed from the filtrate under reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-5fbc38a60a8b492583117380baa374c6
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001909B2

Reaction notes

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