Sodium borohydride → 2,4,6-trimethyl-1H-indene

HRID 1492736Notes

Reaction equation

HRID 1492736 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[C:7]([CH3:11])[CH:8]=2)[C:3]1=O.[BH4-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[C:5]([CH3:12])[CH:6]=[C:7]([CH3:11])[CH:8]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117690492,5,7-Trimethyl-1-indanone

Product 1

HCID 109207862,4,6-trimethyl-1H-indeneYield 96%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

20.4 g (117 mmol) of 2,5,7-trimethyl-l-indanone (1) were dissolved in 300 ml of a mixture of tetrahydrofuran/methanol (2:1), and 6.6 g (175 mmol) of NaBH4 were added at room temperature. The mixture was stirred for a further hour, 50 ml of half-concentrated HC1 were added and the mixture was extracted with ether. The combined organic phases were dried over sodium sulfate and freed from the solvent. The residue was transferred to a distillation apparatus, and 13 g of magnesium sulfate were added. A vacuum of about 10mbar was applied and the mixture was heated up until the product distilled over (130°-150° C). The distillation gave 17.7 g of the indene as a colorless oil. The yield was 96%. Mass spectrum: 158 M+, correct disintegration pattern.

Workup

  1. additionwere added at room temperature
  2. addition50 ml of half-concentrated HC1 were added
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. additionwere added
  6. temperaturethe mixture was heated up until the product
  7. distillationdistilled over (130°-150° C)
  8. distillationThe distillation

Sources & evidence

ORD record
ord-a7b4d189f0ac406d8aab201b9d8e4dbe
Source dataset
uspto-grants-1994_12
Patent number
US05374752

Reaction notes

Loading…