Water → (RS)-2-(2-buten-1-yl)-6-isobutoxy-1-indanone

HRID 264416Notes

Reaction equation

HRID 264416 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)[CH:17]([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH:2]=[CH:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 54363126(RS)-2-(2-buten-1-yl)-6-hydroxy-1-indanone

Product 1

HCID 54374731(RS)-2-(2-buten-1-yl)-6-isobutoxy-1-indanoneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4.74 g of (RS)-2-(2-buten-1-yl)-6-hydroxy-1-indanone, 5.18 ml of isobutyl bromide and 5.98 g of potassium carbonate in 40 ml of N,N-dimethylformamide was heated to 60° for 48 hours. After cooling, the solution was poured into 100 ml of water and extracted twice with 70 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. 5.2 g (93%) of (RS)-2-(2-buten-1-yl)-6-isobutoxy-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 70 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-638846c380fc4d65ae39cc7067e9c389
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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