Tributylphosphine → HCID 90418129, compound

HRID 2177297Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][N:12]=[C:11]([CH3:14])[C:10]=1[CH2:15][OH:16].[F:17][C:18]1[CH:19]=[C:20]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:21]=[C:22]([F:25])[C:23]=1O.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[F:17][C:18]1[CH:19]=[C:20]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:21]=[C:22]([F:25])[C:23]=1[O:16][CH2:15][C:10]1[C:11]([CH3:14])=[N:12][S:13][C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[F:1]

Participants

Conditions

Temperature: 60 °C

Procedure

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed [5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazol-4-yl]methanol (100 mg, 0.42 mmol, 1.00 equiv), ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (146 mg, 0.63 mmol, 1.50 equiv), ADDP (221.6 mg, 0.89 mmol, 2.10 equiv), Bu3P (128 mg, 0.63 mmol, 1.5 equiv), toluene (10 mL). The resulting solution was stirred overnight at 60° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 150 mg (79%) of ethyl 3-(3,5-difluoro-4-[[5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazol-4-yl]methoxy]phenyl) propanoate as colorless oil.

Workup

customInto a 25-mL round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 150 mg (79%) of ethyl 3-(3,5-difluoro-4-[[5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazol-4-yl]methoxy]phenyl) propanoate as colorless oil

Sources & evidence

ORD record: ord-ea0bc50e0e604bbaa733d05f0bb9a4aa
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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