4-Hydroxy-1-indanone → 4-Hydroxyindan

HRID 2178709Notes

Reaction equation

HRID 2178709 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.C([BH3-])#N.[Na+].C[Si](Cl)(C)C>>[CH2:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:2]([OH:1])[C:3]=2[CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 5905474-Hydroxy-1-indanoneHCID 131733031HCID 131733031, compound

Product 1

HCID 742334-Hydroxyindan

Procedure

4-Hydroxy-2,3-dihydro-1H-inden-1-one (W. Liu et al., Org. Lett. 2007, 9, 2915-2918) was reduced with sodium cyanoborohydride/trimethylsilyl chloride to provide 2,3-dihydro-1H-inden-4-ol. This was chlorinated with N-chlorosuccinimide to generate 7-chloro-2,3-dihydro-1H-inden-4-ol.

Sources & evidence

ORD record
ord-962b26a171434dfda36afff40c47869f
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

Loading…