Imidazole → HCID 59780404, compound

HRID 555226Notes

Reaction equation

HRID 555226 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][OH:14])[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.N1C=CN=C1.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:13][O:14][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26])[O:9][CH2:10][CH2:11][O:12]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 66986999[2-(4-Bromophenyl)-1,3-dioxolan-2-yl]methanol

Product 1

HCID 59780404HCID 59780404, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

73.5 g 2-(4-Bromophenyl)-1,3-dioxolane-2-methanol are dissolved in 800 ml N,N-dimethylformamide. 38.6 g imidazole and 51.3 g tert-butyldimethylchlorosilane were added. It was stirred for 12 hours at 23° C. Afterwards, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate. It was stirred for another 30 min. Then it was extracted with ethyl acetate twice. The combined organic layers were washed with brine and dried over sodium sulphate. The crude product was purified by column chromatography. 103.21 g product was obtained (97.5% of theory).

Workup

  1. stirringIt was stirred for another 30 min
  2. extractionThen it was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-344b2260daa74d34999a30cf9e025e24
Source dataset
uspto-grants-2011_11
Patent number
US08053426B2

Reaction notes

Loading…