Imidazole → [(5-Bromo-1,2-dihydro-1-acenaphthylenyl)oxy](tert-butyl)diphenylsilane

HRID 2056735Notes

Reaction equation

HRID 2056735 reaction equation
[Br:1][C:2]1[C:12]2[C:13]3[C:5]([CH2:6][CH:7]([OH:14])[C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.Cl[Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CN=C1>C1COCC1.C(OCC)C>[Br:1][C:2]1[C:12]2[C:13]3[C:5]([CH2:6][CH:7]([O:14][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 687021195-Bromo-1-acenaphthenol

Product 1

HCID 86596013[(5-Bromo-1,2-dihydro-1-acenaphthylenyl)oxy](tert-butyl)diphenylsilane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5-bromo-1,2-dihydro-1-acenaphthylenol (0.25 g, 1 mmol) in dry THF (30 mL) was added chloro(tert-butyl)diphenylsilane (0.275 g, 1 mmol) and imidazole (0.34 g, 5 mmol), and the reaction stirred at room temperature under nitrogen for 18 h. The mixture was diluted with diethyl ether, filtered through a pad of silica, and evaporated in vacuo. Purification by flash chromatography on silica, eluting with ethyl acetate/hexane (1:9 to 1:1), yielded the title compound as a colourless oil.

Workup

  1. filtrationfiltered through a pad of silica
  2. customevaporated in vacuo
  3. customPurification by flash chromatography on silica
  4. washeluting with ethyl acetate/hexane (1:9 to 1:1)

Sources & evidence

ORD record
ord-203a8e6379bf4fbd98494c85637edada
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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