Ethanol → HCID 53711917, compound

HRID 328996Notes

Reaction equation

HRID 328996 reaction equation
[C:1]1([C:7]([CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[CH:8][CH2:9][CH2:10]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25].[OH-].[Na+]>C(OCC)C>[C:1]1([C:7]([CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[CH:8][CH2:9][CH2:10][N:26]([CH2:27][CH3:28])[CH2:24][CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 53808431HCID 53808431, compound

Product 1

HCID 53711917HCID 53711917, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 29.5 g. of 1-phenyl-1-(2-indanyl)-4-chloro-1-butene in 125 cc. of 95 percent (v/v) ethanolbenzene (commercial 2B ethanol) was added 100 cc. of diethylamine in one portion. The reaction mixture was shaken and heated in a sealed bomb to about 100° C for 16 hours. The reaction mixture was cooled to about 25° C. and the solvent was removed under reduced pressure to afford the product as an oily residue. The oil was dissolved in 400 cc. of diethyl ether and shaken with 5N sodium hydroxide and washed with water. The ethereal solution was dried and the solvent was removed under reduced pressure, affording 1-phenyl-1-(2-indanyl)-4-diethylamino-1-butene.

Workup

  1. temperatureThe reaction mixture was cooled to about 25° C.
  2. customthe solvent was removed under reduced pressure
  3. customto afford the product as an oily residue
  4. dissolutionThe oil was dissolved in 400 cc
  5. washwashed with water
  6. customThe ethereal solution was dried
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c69fbea1948a4ea59f80ac47ce69fecf
Source dataset
uspto-grants-1977_04
Patent number
US04018897

Reaction notes

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