3-Chloro-1,1-diphenylpropene → Methyl 2-(3,3-diphenylprop-2-enylthio)-5-trifluoromethylbenzoate

HRID 978097

Reaction equation

HRID 978097 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:16]1([C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:23][CH2:24]Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O1CCCC1>[C:16]1([C:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:23][CH2:24][S:1][C:2]2[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 128901653-Chloro-1,1-diphenylpropeneHCID 13787739Methyl 2-mercapto-5-trifluoromethylbenzoateHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 20205035Methyl 2-(3,3-diphenylprop-2-enylthio)-5-trifluoromethylbenzoateYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.19 g (9.86 mmol) of methyl 2-mercapto-5-trifluoromethylbenzoate, 2.29 g (10.0 mmol) of 1,1-diphenyl-3-chloro-1-propene, and 1.67 g (11.0 mmol) of diazabicycloundecene (DBU) in 10 ml tetrahydrofuran was stirred for 60 minutes at room temperature. The solution was partitioned between ether and water and the ether layer was washed with water, dried over MgSO4 and evaporated. The residue was chromatographed (20% CH2Cl2 -hexane) on silica to afford 3.6 g (85%) of a clear oil. NMR (CDCl3, 90 MHz) 3.67 (d, 2H, J=8, CH2), 3.92 (s, 3H, --OCH3), 6.05 (t, 1H, J=8), 6.9-7.6 (m, 12H), 8.13 (s, 1H).

Workup

  1. customThe solution was partitioned between ether and water
  2. washthe ether layer was washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was chromatographed (20% CH2Cl2 -hexane) on silica

Sources & evidence

ORD record
ord-4a2126e22f1d477a8999c2f6bab1cdc5
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Linked notes

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