HCID 22610224, compound → HCID 20230957, compound

HRID 2290500Notes

Reaction equation

HRID 2290500 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[C:7]2[CH2:6][CH:5]([C:13](O)=[O:14])[CH2:4][C:3]1=2.[CH3:17][Li]>O1CCCC1>[CH3:17][C:13]([CH:5]1[CH2:4][C:3]2[C:2]([CH3:16])([CH3:1])[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[C:7]=2[CH2:6]1)=[O:14]

Participants

4

Reactant 2

HCID 22610224HCID 22610224, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20230957HCID 20230957, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.3 g of 4,5,6,7-tetrahydro-4,4,7,7-tetramethyl-2-indanecarboxylic acid are dissolved in 150 ml of tetrahydrofuran and treated slowly while cooling with ice and stirring vigorously with 47.3 ml of methyl lithium (1.6 molar in ether). After stirring for 3 hours at room temperature, the mixture is poured on to ice, extracted with ether, washed with water, dried over sodium sulphate and evaporated. After distillation of the crude product, there are obtained 5.6 g of 2,2,5,5-tetramethyl-bicyclo[4.3.0]non-1(6)-en-8-yl methyl ketone as a colourless liquid of boiling point 53°-60° C./0.01 mm Hg.

Workup

  1. additiontreated slowly
  2. temperaturewhile cooling with ice
  3. additionthe mixture is poured on to ice
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. distillationAfter distillation of the crude product, there

Sources & evidence

ORD record
ord-6d0b458a3e624161911a42370cf319a4
Source dataset
uspto-grants-1986_10
Patent number
US04617146

Reaction notes

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