Triphenylphosphine → {4-[3,3-Bis-(3-methyl-thiophen-2-yl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

HRID 1247685Notes

Reaction equation

HRID 1247685 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])=[CH:8][CH2:9]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH2:48]([O:50][C:51](=[O:65])[CH2:52][O:53][C:54]1[CH:59]=[CH:58][C:57]([SH:60])=[CH:56][C:55]=1[C:61]([F:64])([F:63])[F:62])[CH3:49]>C1COCC1>[CH2:48]([O:50][C:51](=[O:65])[CH2:52][O:53][C:54]1[CH:59]=[CH:58][C:57]([S:60][CH2:9][CH:8]=[C:7]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[CH3:16])[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])=[CH:56][C:55]=1[C:61]([F:62])([F:63])[F:64])[CH3:49]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 219076783,3-Bis-(3-methylthiophen-2-yl)-prop-2-en-1-olHCID 59516001Ethyl [4-sulfanyl-2-(trifluoromethyl)phenoxy]acetate

Product 1

HCID 68575646{4-[3,3-Bis-(3-methyl-thiophen-2-yl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,3-bis-(3-methyl-thiophen-2-yl)-prop-2-en-1-ol (110 mg, 0.44 mmol) and triphenylphosphine (220 mg, 0.88 mmol) in THF was added, at room temperature and under nitrogen atmosphere, DEAD (153 mg, 0.88 mmol). The reaction mixture was stirred for 5 min after which (2-trifluoromethyl-4-mercapto-phenoxy)-acetic acid ethyl ester (70 mg, 0.25 mmol) was added over 15 min. The reaction mixture was stirred at room temperature for 100 hours. The reaction mixture was evaporated and the crude residue was purified on a Horizon using a methylene chloride:heptanes gradient as eluent. The desired {4-[3,3-bis-(3-methyl-thiophen-2-yl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester was isolated in 75 mg (59%) yield.

Workup

  1. additionwas added over 15 min
  2. customThe reaction mixture was evaporated
  3. customthe crude residue was purified on a Horizon

Sources & evidence

ORD record
ord-a210a5d02894405799986db20db6f12d
Source dataset
uspto-grants-2006_10
Patent number
US07129268B2

Reaction notes

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