Cyclobuta[a]naphthalen-1(2H)-one → 1,2-Dihydrocyclobuta[a]naphthalen-1-ol

HRID 2229437Notes

Reaction equation

HRID 2229437 reaction equation
[BH4-].[Na+].[C:3]1(=[O:15])[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[CH2:4]1)[CH:11]=[CH:10][CH:9]=[CH:8]3>CO>[CH:3]1([OH:15])[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[CH2:4]1)[CH:11]=[CH:10][CH:9]=[CH:8]3

Participants

4

Reactant 2

HCID 2752742Cyclobuta[a]naphthalen-1(2H)-oneHCID 4311764Sodium borohydride

Product 1

HCID 184677691,2-Dihydrocyclobuta[a]naphthalen-1-olYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.4 g of sodium borohydride are added to a suspension, at 0-5° C., of 5.2 g of the product obtained in Step 2 in 150 ml of methanol. After 15 minutes at that temperature and then 1 hour at room temperature, the reaction mixture is poured into 300 g of ice and extracted with dichloromethane. After customary treatment, 5.2 g of the expected product are isolated.

Workup

  1. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-24428f2ff60d48efbf916c66ea6159ef
Source dataset
uspto-grants-2002_07
Patent number
US06420413B2

Reaction notes

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