Imidazole → HCID 57036210, compound

HRID 129867Notes

Reaction equation

HRID 129867 reaction equation
[CH3:1][O:2][C:3]1[CH2:8][CH:7]=[C:6]([CH2:9][CH2:10][OH:11])[CH2:5][CH:4]=1.N1C=CN=C1.[Si:17](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH2:8][CH:7]=[C:6]([CH2:9][CH:10]([OH:11])[Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:5][CH:4]=1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 12400614HCID 12400614, compound

Product 1

HCID 57036210HCID 57036210, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude compound (1) was dissolved in N,N-dimethylformamide (150 mL) and treated at room temperature with imidazole (44.8 g, 658 mmol) and t-butyldiphenylsilyl chloride (85.6 mL, 329 mmol). The resulting solution was stirred at room temperature for 2 d (reaction was essentially complete after a few hours) after which time it was diluted with 10% ethyl acetate in hexane, washed 3× with water, dried over anhydrous MgSO4, filtered and evaporated to give crude 1-methoxy-4-[2-(t-butyldiphenylsilyl)hydroxyethyl]-cyclohexa-1,4-diene (3). The mixture, which was contaminated with the over-reduced product 4-[2-(t-butyldiphenylsilyl)hydroxyethyl]-cyclohex-1-ene (4), was used in the next step without further purification. Compound (3): 1H NMR (CDCl3) δ 1.07 (9H, s), 2.25 (2H, t, J=6.0 Hz), 2.70 (4H, s), 3.55 (3H, s), 3.77 (2H, t, J=6.0 Hz), 4.62 (1H, br s), 5.43 (1H, br s), 7.22-7.93 (10H, m).

Workup

  1. customreaction
  2. waitwas essentially complete after a few hours
  3. washwashed 3× with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-88e7504e2ba447529c2b61b32ef83378
Source dataset
uspto-grants-1995_11
Patent number
US05470849

Reaction notes

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