Imidazole → HCID 68858628, compound

HRID 553575Notes

Reaction equation

HRID 553575 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([OH:9])[CH2:4]1.[Si:10](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CN=C1.CN(C1C=CC=CN=1)C>CN(C)C=O>[Si:10]([O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([OH:9])[CH2:4]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 218852-DimethylaminopyridineHCID 94078tert-ButyldiphenylchlorosilaneHCID 67460753HCID 67460753, compound

Product 1

HCID 68858628HCID 68858628, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.5 g of (1S,3R)/(1R,3S)-3-hydroxymethylcyclohexanol are dissolved in 300 ml of dimethylformamide, and 23 ml of tert-butyldiphenylsilanyl chloride, 8.0 g of imidazole and 200 mg of dimethylaminopyridine are added. The mixture is stirred at room temperature for 12 hours. The dimethylformamide is removed under reduced pressure and the residue is dissolved in 300 ml of ethyl acetate and washed five times with in each case 100 ml of water. The organic phase is dried over MgSO4 and the solvent is then removed under reduced pressure. This gives 27.0 g of (1S,3R)/(1R,3S)-3-(tert-butyldiphenylsilanyloxymethyl)cyclohexanol as an oil. C23H32O2Si (368.6), Rf(n-heptane:ethyl acetate=1:1)=0.42.

Workup

  1. customThe dimethylformamide is removed under reduced pressure
  2. dissolutionthe residue is dissolved in 300 ml of ethyl acetate
  3. washwashed five times with in each case 100 ml of water
  4. dry with materialThe organic phase is dried over MgSO4
  5. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-9cdcb7c833ea4069a1355a959ebf51aa
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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