Acetophenone → 3-(Methylsulfanyl)-1,5-diphenylpent-2-ene-1,5-dione

HRID 544753Notes

Reaction equation

CS[C:3]([S:13][CH3:14])=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9]N=1)=[O:6].[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[CH3:16].[CH3:24]C(C)([O-])C.[K+]>C1COCC1>[C:7]1([C:5](=[O:6])[CH:4]=[C:3]([S:13][CH3:14])[CH2:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[CH:24]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Ketene dithioacetal (Product A) (2.0 g, 0.0089 mol) was added to a solution of acetophenone (1.07 g, 0.0089 mol) and potassium tert-butoxide (2.0 g, 0.0178 mol) in dry THF (20 mL). The temperature of the reaction mixture was raised to 60° C. and the mixture was stirred for 1 hour during which time an orange-red precipitate formed. This was collected and added to an ice-cold HCl solution (4% acid) and the oily material which separated allowed to crystallize. The brown solid was collected and recrystallized from benzene: petroleum ether (b.p. 80°-100° C.) from which it separated as pale-yellow prisms: 1.8 g (70%), m.p. 106°-108° C.: IR (KBr)νCO 1680, 1630 cm-1 ; NMR (CDCl3)δ8.0-7.56 (m, 10, aromatic), 6.82 (s,1, vinylic), 4.64 (s,2,CH2), 2.59 (s,3,SCH3); M.+ 296 (7%).

Workup

customformed
customThis was collected
additionadded to an ice-cold HCl solution (4% acid)
customthe oily material which separated
customto crystallize
customThe brown solid was collected
customrecrystallized from benzene
custompetroleum ether (b.p. 80°-100° C.) from which it separated as pale-yellow prisms

Sources & evidence

ORD record: ord-2d23311ef4ba47ad94a601a85435084a
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04451659

Reaction notes

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