N,N-Dimethylglycine → trans-Stilbene

HRID 429610

반응식

HRID 429610 반응식
CN(C)[CH2:3][C:4](O)=O.[C:8]([O-])(=O)[CH3:9].[Na+].CN1[C:18](=O)[CH2:17][CH2:16][CH2:15]1.[CH2:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].C(OCC)C>[C:22]1(/[CH:21]=[CH:20]/[C:4]2[CH:3]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:22]1(/[CH:21]=[CH:20]\[C:8]2[CH:9]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:22]1([C:21]([C:4]2[CH:3]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH2:20])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

9

반응물 4

HCID 673N,N-DimethylglycineHCID 7501StyreneHCID 13387N-methyl-2-pyrrolidone2회HCID 517045Sodium Acetate

생성물 3

HCID 107401,1-DiphenylethyleneHCID 638088trans-Stilbene수율 97.4%HCID 5356785cis-Stilbene수율 0.6%

시약·촉매·용매 2

HCID 164911Tetraphenylphosphonium Chloride촉매HCID 3283Diethyl Ether용매

실험 절차

To a reaction vessel standing on a scale which is sealed with a septum cap, 5.3 mg (0.02 mmol) of (CH3CN)2PdCl2, 45 mg (0.12 mmol) of Ph4PCl and 12.4 mg (0.12 mmol) of dimethylglycine are added, followed by two cycles of evacuation and flushing with argon. Under argon, 657.7 mg (8 mmol) of anhydrous sodium acetate and 1 ml of NMP are added. 452 mg (4.01 mmol) of Cl-benzene and 636 mg (6.11 mmol) of styrene is mixed with 1 ml of NMP and added dropwise in 6 portions within 6 hours, the first portion being added at room temperature and the others at 140° C. Stirring is performed at 140° C. for a total of 24 h. According to the processing described in Example 1 using 10 ml of diethyl ether, a 64.2% yield of Heck products (97.4% trans-stilbene, 0.6% cis-stilbene, and 2.0%- 1,1-diphenylethene) is obtained with 76.6% conversion of Cl-benzene.

후처리

  1. customTo a reaction vessel standing on a scale which
  2. customis sealed with a septum
  3. customcap
  4. customflushing with argon
  5. additionadded dropwise in 6 portions within 6 hours
  6. additionthe first portion being added at room temperature
  7. customat 140° C
  8. customis performed at 140° C. for a total of 24 h

출처 및 근거

ORD 기록
ord-d92d3569a6cc478798316003861e97d6
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316675B1

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