Sodium borohydride → HCID 18792598, compound

HRID 357670Notes

Reaction equation

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

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 18792603HCID 18792603, compound

Product 1

HCID 18792598HCID 18792598, compoundYield 65%

Procedure

Analogously to Example D, 1.50 g (8 mmol) of 2,5,6,7-tetramethyl-1-indanone (9) were reduced with 0.45 g (12 mmol) of NaBH4. The alcohol, which was not purified further, was then further reacted in the presence of 0.1 g of p-toluenesulfonic acid in 100 ml of toluene. Chromatography on 100 g of silica gel (hexane/methylene chloride 9:1) gave 0.88 g (65%) of 2,4,5,6-tetramethylindene (10).

Workup

customThe alcohol, which was not purified further
customwas then further reacted in the presence of 0.1 g of p-toluenesulfonic acid in 100 ml of toluene

Sources & evidence

ORD record: ord-9cf64e0536944ddb9245799a2d287a48
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840948

Reaction notes

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