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

HRID 978097

반응식

HRID 978097 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4a2126e22f1d477a8999c2f6bab1cdc5
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04663344

연결된 노트

불러오는 중…