Sodium borohydride → HCID 18314750, compound

HRID 357668Notes

Reaction equation

HRID 357668 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:8]=2)[C:3]1=O.[BH4-].[Na+]>>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[C:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:8]=2

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 18314753HCID 18314753, compound

Product 1

HCID 18314750HCID 18314750, compoundYield 95%

Procedure

Analogously to Example D, 8.3 g (41 mmol) of 2-methyl-5-isobutyl-1-indanone (7) were reduced with 2.4 g (62 mmol) of NaBH4. The alcohol, which was not purified further, was then further reacted in the presence of 0.4 g of p-toluenesulfonic acid in 100 ml of toluene at 80° C. Chromatography on 400 g of silica gel (hexane) gave 7.17 g (95%) of 2-methyl-6-insobutylindene (8).

Workup

  1. customThe alcohol, which was not purified further
  2. customwas then further reacted in the presence of 0.4 g of p-toluenesulfonic acid in 100 ml of toluene at 80° C

Sources & evidence

ORD record
ord-44018ecb84d344b49018f87625ff8120
Source dataset
uspto-grants-1998_11
Patent number
US05840948

Reaction notes

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