Acetyl chloride → HCID 69544485, compound

HRID 1813942Notes

Reaction equation

HRID 1813942 reaction equation
C([O:8][CH2:9][CH2:10][C:11]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)=[C:12]([C:19]1[CH:30]=[CH:29][C:22]([O:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1.C(Cl)(=O)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.[Zn]>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:11](=[C:12]([C:19]2[CH:20]=[CH:21][C:22]([O:23][CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])=[CH:29][CH:30]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH2:9][OH:8])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 8857Ethyl AcetateHCID 69544363HCID 69544363, compound

Product 1

HCID 69544485HCID 69544485, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

(2-{4-[4-Benzyloxy-2-(4-chlorophenyl)-1-phenylbut-1-enyl]phenoxy}ethyl)dimethylamine (1.1 g, 2.1 mmol) is dissolved in toluene, Zn powder (0.4 g, 6.1 mmol) and acetyl chloride (0.6 g, 7.6 mmol) are added and the mixture is stirred at 40° C. for 3 h. Additional Zn (0.5 g) and acetyl chloride (0.6 g) are added and stirring is continued for another 5 h. Ethyl acetate is added and the precipitate is filtered off. The solvents are evaporated and the residue is dissolved in methanol. The acetate ester of the product is hydrolyzed by making the mixture alkaline with 48% aqueous sodium hydroxide and stirring the mixture at room temperature for 2 h. Methanol is evaporated, the residue is dissolved in toluene and washed with water. Toluene is evaporated and the isomers of the product are separated by flash chromatography. The yield of the Z-isomer is 0.25 g and of the E-isomer 0.15 g.

Workup

  1. stirringstirring
  2. waitis continued for another 5 h
  3. filtrationthe precipitate is filtered off
  4. customThe solvents are evaporated
  5. dissolutionthe residue is dissolved in methanol
  6. stirringstirring the mixture at room temperature for 2 h
  7. customMethanol is evaporated
  8. dissolutionthe residue is dissolved in toluene
  9. washwashed with water
  10. customToluene is evaporated
  11. customthe isomers of the product are separated by flash chromatography

Sources & evidence

ORD record
ord-cd4956053a444231a8bf7555b230b09d
Source dataset
uspto-grants-2005_04
Patent number
US06875775B2

Reaction notes

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