Imidazole → HCID 58018637, compound

HRID 2427471Notes

Reaction equation

HRID 2427471 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.N1C=CN=C1.[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)C>CN(C=O)C>[CH2:11]([O:10][C:8]([CH:5]1[CH2:4][CH2:3][CH:2]([O:1][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7][CH2:6]1)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 94078tert-ButyldiphenylchlorosilaneHCID 178472487HCID 178472487, compound

Product 1

HCID 58018637HCID 58018637, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a solution of cis/trans ethyl 4-hydroxycyclohexanecarboxylate (21.3 g, 0.124 mol) and imidazole (10.10 g, 0.148 mol) in DMF (150 mL) with t-butyl-diphenylsilyl chloride (37.39 g, 0.136 mol) and stir for 72 hours at room temperature. Dilute the reaction with diethyl ether and wash with 1N HCl and water. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product. Purify with a 0 to 20% ethyl acetate in hexanes gradient on silica gel to afford 40.4 g (80%) of the titled product. Rf=0.49 and 0.29 (5/1 hexanes/ethyl acetate).

Workup

  1. additionDilute
  2. washwash with 1N HCl and water
  3. dry with materialDry the organic layer with Na2SO4
  4. customremove the solvent in vacuo
  5. customto afford crude product
  6. customPurify with a 0 to 20% ethyl acetate in hexanes gradient on silica gel

Sources & evidence

ORD record
ord-ffd88e9dd93047fd9591f55823093a3b
Source dataset
uspto-grants-2011_06
Patent number
US07968585B2

Reaction notes

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