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

HRID 978097

反応式

HRID 978097 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4a2126e22f1d477a8999c2f6bab1cdc5
出典データセット
uspto-grants-1987_05
特許番号
US04663344

関連ノート

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