Dioctylamine → 4,4'-Bis-dioctylaminostilbene

HRID 1387193

반응식

HRID 1387193 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:17]1([CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1P.C[C:26]([CH3:29])([O-])[CH3:27].[Na+].[CH2:31]([NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:31]([N:39]([CH2:40][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:17][CH3:24])[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N:39]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:27][CH2:26][CH3:29]

참가 물질

7

반응물 4

HCID 3094DioctylamineHCID 15049146(2-Methylphenyl)phosphaneHCID 23676156Sodium t-butoxideHCID 533959814,4'-Dibromostilbene

생성물 1

HCID 544306514,4'-Bis-dioctylaminostilbene

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

An oven dried 3-necked flask was fitted with a reflux condenser and purged with nitrogen. Into the flask was placed 4,4′-dibromostilbene (1.0 g, 2.96 mmol) (synthesized by the general Wittig procedure described above), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (13.5 mg, 0.0148 mmol), o-tolylphosphine (13,5 mg, 0.044 mmol), and sodium t-butoxide (711 mg, 7.4 mmol) in 6 mL dry toluene. Dioctylamine (1.608 g, 6.65 mmol) was then added and the reaction mixture was stirred for 48 hours at 80° C. under nitrogen balloon atmosphere. The crude product was then adsorbed onto silica gel and purified via flash chromatography with gradual elutions from 98/2 to 95/5 (hexanes:ethyl acetate). 1H NMR (d6-acetone) δ 0.89 (m, 12H), 1.20-1.70 (m, 24H), 3.34 (t, J=7.51 Hz, 8H), 6.66 (d, J=8.75 Hz, 4H), 6.83 (s, 2H), 7.32 (d, J=8.62 Hz, 4H).

후처리

  1. customAn oven dried 3-necked flask
  2. customwas fitted with a reflux condenser
  3. custompurged with nitrogen
  4. customsynthesized by the general Wittig procedure
  5. custompurified via flash chromatography with gradual elutions from 98/2 to 95/5 (hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-58b9ac06f54b4d3f9a26e1f190c6aa6b
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06267913B1

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