Imidazole → HCID 18993691, compound

HRID 375775Notes

Reaction equation

HRID 375775 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH2:12][CH2:13][CH2:14][OH:15])[CH:9]([OH:16])[CH2:8][CH2:7]2.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH2:12][CH2:13][CH2:14][O:15][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:9]([OH:16])[CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18993688HCID 18993688, compound

Product 1

HCID 18993691HCID 18993691, compoundYield 107.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 8-bromo-1,2,3,4-tetrahydro-1-(3-hydroxypropyl)-2-hydroxynaphthalene (B-3, 29.15 g, 0.10 mol) and imidazole (17.02 g, 0.25 mol) in dimethylformamide (70 mls) was cooled in ice, and t-butyldimethylsilyl chloride (17.3 g, 0.115 mol) was added with stirring. The mixture was allowed to warm to room temperature slowly. After stirring for a total of 18 hours, crushed ice (30 mls) was added, and the mixture was stirred at ambient temperature for 0.5 hour. The mixture was diluted with water (300 mls) and extracted twice with 1:1 diethylether/hexane. The extracts were washed twice with water and once with brine. The solution was dried (MgSO4), and the solvent was removed under vacuum to leave the title compound as an oil (B-4, 42.78 g, 100%). NMR (CDCl3, TMS)δ0.083, 0.099 (twos,6H,Si-CH3), 0.91 (s,9H,Si-tBu), 1.50-1.60(m, 1H), 1.8-2.0(m,5H), 2.8-3.0(m,2H), 3.19 (d,J=4.3 Hz, 1H), 3.48(m,5 lines, 1H), 3.65-3.85 (m,2H), 4.0-4.13 (m,1H), 6.86(t,J=7.6 Hz, 1H), 6.93 (br. d,J=7.6 Hz, 1H), 7.30 (br. d,J=7.5 Hz,1H). IR (Major peaks)3411, 3057, 1592, 1559, 1472, 1463, 1438, 1256, 1100, 1067, 835, 774. CI Mass spec. m+at m/z 399,401.

Workup

  1. stirringAfter stirring for a total of 18 hours
  2. additionwas added
  3. stirringthe mixture was stirred at ambient temperature for 0.5 hour
  4. extractionextracted twice with 1:1 diethylether/hexane
  5. washThe extracts were washed twice with water and once with brine
  6. dry with materialThe solution was dried (MgSO4)
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3499aae033724777bf49ed901b7855a8
Source dataset
uspto-grants-1996_01
Patent number
US05486611

Reaction notes

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