Tributylphosphine → HCID 67146546, compound

HRID 1810693Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)=[CH:9]\[CH2:10][OH:11])=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH3:57][O:58][C:59](=[O:70])[CH2:60][O:61][C:62]1[CH:67]=[CH:66][C:65](O)=[CH:64][C:63]=1[CH3:69]>O1CCCC1>[CH3:57][O:58][C:59](=[O:70])[CH2:60][O:61][C:62]1[CH:67]=[CH:66][C:65]([O:11][CH2:10]/[CH:9]=[C:8](\[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)/[C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:13]=2)=[CH:64][C:63]=1[CH3:69]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the above alcohol (100 mg, 0.305 mmol) in dry tetrahydrofuran (20 ml), was added tributylphosphine (0.11 ml, 0.61 mmol). The mixture was cooled to 0° C. and added 1,1′-(azodicarbonyl)dipiperidine (153 mg, 0.61 mmol), and after 10 min. (4-hydroxy-2-methyl-phenoxy)-acetic acid methyl ester (65 mg, 0.34 mmol) were added. The reaction mixture was stirred for 1.5 hours at 0° C. and then allowed to warm up to ambient temperature overnight. To the reaction mixture was added silica gel Fluka 60 (10 g) and the reaction mixture was evaporated in vacuo. The residue was purified by ISCO combiflash 16 (silica gel, hexane/ethyl acetate 85:15) giving {4-[(Z)-3-(4-fluoro-phenyl)-3-(4-phenylethynyl-phenyl)-allyloxy]-2-methyl-phenoxy}-acetic acid methyl ester as an oil.

Workup

temperatureto warm up to ambient temperature overnight
customthe reaction mixture was evaporated in vacuo
customThe residue was purified by ISCO combiflash 16 (silica gel, hexane/ethyl acetate 85:15)

Sources & evidence

ORD record: ord-556c7dcbdc764748bc0167a5553af7de
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362016B2

Reaction notes

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