Tributylphosphine → HCID 90406160, compound

HRID 1404179Notes

Reaction equation

[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[C:8]2[CH2:16][OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:22]=[C:23]([F:26])[C:24]=1O.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[F:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:22]=[C:23]([F:26])[C:24]=1[O:17][CH2:16][C:8]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=[CH:10][C:9]=1[C:12]([F:13])([F:14])[F:15]

Participants

Conditions

Temperature: 60 °C

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed [1-phenyl-3-(trifluoromethyl)-1H-pyrrol-2-yl]methanol (260 mg, 1.05 mmol, 1.00 equiv, 97%), ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (281 mg, 1.22 mmol, 1.20 equiv), ADDP (642 mg, 2.56 mmol, 2.50 equiv), Bu3P (309 mg, 1.53 mmol, 1.50 equiv) and toluene (5 mL). The resulting solution was stirred overnight at 60° C. in an oil bath. The resulting mixture was then concentrated under vacuum. The resulting mixture was washed with diethyl ether (50 mL). The resulting residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5) to yield ethyl 3-(3,5-difluoro-4-[[1-phenyl-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy]phenyl)propanoate as yellow oil (220 mg, 45%).

Workup

customInto a 50-mL round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
concentrationThe resulting mixture was then concentrated under vacuum
washThe resulting mixture was washed with diethyl ether (50 mL)

Sources & evidence

ORD record: ord-670ce99221dd42bea5e1532c9e612282
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912227B1

Reaction notes

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