N,N-Dimethylglycine → trans-Stilbene

HRID 429610

反応式

HRID 429610 の反応式
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

参加物

9

反応物 4

HCID 673N,N-DimethylglycineHCID 7501StyreneHCID 13387N-methyl-2-pyrrolidone2 回HCID 517045Sodium Acetate

生成物 3

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

試薬・触媒・溶媒 2

HCID 164911Tetraphenylphosphonium Chloride触媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d92d3569a6cc478798316003861e97d6
出典データセット
uspto-grants-2001_11
特許番号
US06316675B1

関連ノート

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