Imidazole → 6-Hydroxy-1-indanone

HRID 2306230Notes

Reaction equation

HRID 2306230 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[Si:12](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CN=C1>CN(C=O)C>[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[Si:12]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 70206596-Hydroxy-1-indanone

Product 2

HCID 70206596-Hydroxy-1-indanoneHCID 11047330HCID 11047330, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

6-Hydroxy-1-indanone was prepared according to the procedure described by Nayak & Chakraborti, Tetrahedron Lett., 38, 8749-8752 (1997). A mixture of 6-hydroxy-1-indanone (5.00 g, 33.8 mmol), tert-butyldiphenylsilyl chloride (23.1 g, 84.2 mmol), and imidazole (6.90 g, 101.4 mmol) in degassed DMF (100 mL) was heated at 60° C. for 18 hours. The solvent was removed in vacuo and the residue purified by silica gel chromatography, eluting with a gradient of hexane—10% to 15% EtOAc, to yield the titled product.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by silica gel chromatography
  3. washeluting with a gradient of hexane—10% to 15% EtOAc

Sources & evidence

ORD record
ord-6a862660befe4f90b3b186e07faf0a3d
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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