N,N-Dimethylglycine → trans-Stilbene

HRID 429610

Reaction equation

HRID 429610 reaction equation
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

Participants

9

Reactant 4

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

Product 3

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

Reagents, catalysts & solvents 2

HCID 164911Tetraphenylphosphonium ChlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d92d3569a6cc478798316003861e97d6
Source dataset
uspto-grants-2001_11
Patent number
US06316675B1

Linked notes

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