Imidazole → HCID 21107236, compound

HRID 1870029Notes

Reaction equation

HRID 1870029 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH2:7][CH2:6][C:5]2([CH3:15])[CH3:14].N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].O>CN(C)C=O>[C:24]([Si:21]([CH3:23])([CH3:22])[O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH2:7][CH2:6][C:5]2([CH3:15])[CH3:14])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 21107232HCID 21107232, compound2×

Product 1

HCID 21107236HCID 21107236, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-hydroxy-4,4,7-trimethyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 171, 2.04 g, 10 mmol) in anhydrous N,N-dimethyl formamide (10 mL) under argon was treated with imidazole (1 g, 14.7 mmol) followed by tert-butyldimethylsilyl chloride (1.5 g, 10 mmol). After stirring the reaction mixture at ambient temperature overnight, it was poured into water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to a residue that was purified by flash column chromatography on silica gel (230-400 mesh) using 8-14% ethyl acetate in hexane as the eluent to afford the title compound (2.5 g, 79%).

Workup

  1. extractionextracted with diethyl ether (×2)
  2. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated to a residue that
  5. customwas purified by flash column chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-8b9d825f3ace410d8ad0163dd8d6c1df
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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