Tributylphosphine → (4-{(e)-3-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-3-phenyl-allyloxy}-2-methyl-phenoxy)-acetic acid methyl ester

HRID 1810696Notes

Reaction equation

[CH3:1][N:2]([CH3:22])[CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13]/[CH2:14][OH:15])=[CH:8][CH:7]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH3:54][O:55][C:56](=[O:67])[CH2:57][O:58][C:59]1[CH:64]=[CH:63][C:62](O)=[CH:61][C:60]=1[CH3:66]>O1CCCC1>[CH3:54][O:55][C:56](=[O:67])[CH2:57][O:58][C:59]1[CH:64]=[CH:63][C:62]([O:15][CH2:14]/[CH:13]=[C:12](/[C:9]2[CH:10]=[CH:11][C:6]([C:5]#[C:4][CH2:3][N:2]([CH3:1])[CH3:22])=[CH:7][CH:8]=2)\[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:61][C:60]=1[CH3:66]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the above alcohol (407 mg, 1.397 mmol) in dry tetrahydrofuran (40 mL) was added tributylphosphine (0.50 ml, 2.79 mmol). To the mixture was cooled to 0° C. and added 1,1′-(azodicarbonyl)dipiperidine (703 mg, 2.79 mmol) and after 10 min. (4-hydroxy-2-methyl-phenoxy)-acetic acid methyl ester (301 mg, 1.536 mmol) was added. After stirring for 1.5 hr at 0° C. the mixture was allowed to warm up to ambient temperature and stirred overnight. The reaction mixture was added silica gel Fluka 60 (10 g) and evaporated in vacuo. The residue was purified by ISCO combiflash 16 (silica gel, hexane/ethyl acetate 85:15) giving (4-{(E)-3-[4-(3-dimethylamino-prop-1-ynyl)-phenyl]-3-phenyl-allyloxy}-2-methyl-phenoxy)-acetic acid methyl ester as an oil.

Workup

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

Sources & evidence

ORD record: ord-b7fd5185cef04bf99d9082ef9d67c464
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362016B2

Reaction notes

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