Dimethylformamide → (RS)-2-(2-buten-1-yl)-6-ethoxy-1-indanone

HRID 264412Notes

Reaction equation

HRID 264412 reaction equation
[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([OH:14])=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH:2]=[CH:3][CH3:4].[CH2:16](Br)[CH3:17].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(C)=O.O>[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH2:16][CH3:17])=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH:2]=[CH:3][CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 54363126(RS)-2-(2-buten-1-yl)-6-hydroxy-1-indanone

Product 1

HCID 53729864(RS)-2-(2-buten-1-yl)-6-ethoxy-1-indanoneYield 98%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 5.0 g of (RS)-2-(2-buten-1-yl)-6-hydroxy-1-indanone, 4.1 ml of ethyl bromide, 6.83 g of potassium carbonate and 10 ml of N,N-dimethyl-formamide in 70 ml of acetone was heated to 35° for 35 hours. After cooling, the solution was poured into 100 ml of water and extracted twice with 100 ml of ethyl acetate each time. The combined organic phases were washed once with 70 ml of water and once with 70 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. 5.6 g (98%) of (RS)-2-(2-buten-1-yl)-6-ethoxy-1-indanone were obtained as a red-brown oil which was used directly in the next reaction.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with 100 ml of ethyl acetate each time
  3. washThe combined organic phases were washed once with 70 ml of water and once with 70 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationthe solution was concentrated in a vacuum

Sources & evidence

ORD record
ord-b879e159d2af41e68e730dc1dc95d348
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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