Tributylphosphine → Ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate

HRID 9689Notes

Reaction equation

HRID 9689 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][CH:12]=[C:11]([CH2:14]O)[CH:10]=2)=[CH:5][CH:4]=1.C(P(CCCC)CCCC)CCC.[CH2:31]([O:33][C:34](=[O:45])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([SH:43])=[CH:39][C:38]=1[CH3:44])[CH3:32]>O1CCCC1>[CH2:31]([O:33][C:34](=[O:45])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([S:43][CH2:14][C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=3)[O:13][CH:12]=2)=[CH:39][C:38]=1[CH3:44])[CH3:32]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetateHCID 21986330{5-[4-(Trifluoromethyl)phenyl]-3-furyl}methanol

Product 1

HCID 21986477Ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of {5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol (0.15 g) in tetrahydrofuran (15 ml) stirred at 0° C. was treated with tributylphosphine (0.2 ml), as solution of ethyl(4-mercapto-2-methylphenoxy)acetate (0.150 g) in tetrahydrofuran (2 ml) and finally azodicarbonyldimorpholide (0.204 g). The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The solvent was evaporated and the residue subjected to an aqueous work up using ethyl acetate and water. The organic phase was dried over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using a cyclohexane:ethyl acetate (5:1) as eluent to give the title compound.

Workup

  1. customThe solvent was evaporated
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customThe product isolated
  4. customafter evaporation of the solvent
  5. customwas further purified by flash column chromatography

Sources & evidence

ORD record
ord-e19001d0595c45359652e9e2aef71108
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Reaction notes

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