Imidazole → 3-(5-Fluorobenzothiazol-2-yl-trans-ethenyl)benzyl alcohol t-butyldimethylsilyl ether

HRID 1109782Notes

Reaction equation

HRID 1109782 reaction equation
CN(C)C=O.[F:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13](/[CH:15]=[CH:16]/[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[CH2:20][OH:21])=[N:12][C:11]=2[CH:25]=1.N1C=CN=C1.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>C(OCC)(=O)C>[Si:31]([O:21][CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17](/[CH:16]=[CH:15]/[C:13]2[S:14][C:10]3[CH:9]=[CH:8][C:7]([F:6])=[CH:25][C:11]=3[N:12]=2)[CH:18]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 678284333-(5-Fluorobenzothiazol-2-yl-trans-ethenyl)benzyl alcohol

Product 1

HCID 678284583-(5-Fluorobenzothiazol-2-yl-trans-ethenyl)benzyl alcohol t-butyldimethylsilyl ether

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 100 ml of dimethylformamide containing 2.0 g of 3-(5-fluorobenzothiazol-2-yl-trans-ethenyl)benzyl alcohol and 1.19 g of imidazole was added 1.37 g of t-butyldimethylsilyl chloride and the reaction mixture stirred overnight under nitrogen at room temperature. After 48 hours of reaction time, the mixture was poured into 500 ml of ethyl acetate and washed with water (3×150 ml), a 1N hydrochloric acid solution (2×150 ml), water (1×200 ml) and a brine solution (1×200 ml) The organic layer was separated, dried over sodium sulfate and concentrated to a white solid. The residue was recrystallized from ethyl acetate--hexane, 1.57 g, m.p. 91°-93° C.

Workup

  1. customAfter 48 hours of reaction time
  2. washwashed with water (3×150 ml)
  3. customa 1N hydrochloric acid solution (2×150 ml), water (1×200 ml) and a brine solution (1×200 ml) The organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a white solid
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0cbd098b16414b04ae6aeb6c99f27398
Source dataset
uspto-grants-1994_06
Patent number
US05322847

Reaction notes

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