Imidazole → HCID 69054406, compound

HRID 2102985Notes

Reaction equation

HRID 2102985 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7](=[O:14])[CH2:6][CH2:5]2.[CH:16]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C.C(OCC)(=O)C>[CH3:15][C:3]1[C:2]([O:1][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:16]([CH3:18])[CH3:17])=[C:11]([CH3:12])[C:10]([CH3:13])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:14])[O:8]2

Participants

6

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 2973756-hydroxy-5,7,8-trimethyl-chroman-2-one

Product 1

HCID 69054406HCID 69054406, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-hydroxy-5,7,8-trimethyl-chroman-2-one (1.22 g), triisopropylsilyl chloride (1.71 g) and imidazole (806 mg, 11.84 mmol) in anhydrous DMF (2 mL) was stirred at room temperature for two days. The solution was diluted with ethyl acetate, washed with water and brine. Evaporation and chromatography (silica gel, hexane-ethyl acetate) gave 1.25 g of 5,7,8-trimethyl-6-triisopropylsilanyloxy-chroman-2-one.

Workup

  1. washwashed with water and brine
  2. customEvaporation and chromatography (silica gel, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cd7a2b93766740c7b3252c25ac105b11
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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