Imidazole → HCID 67267363, compound

HRID 1367676Notes

Reaction equation

HRID 1367676 reaction equation
[CH2:1]([Si:3](Cl)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH2:9]([O:11][C:12]([C@@H:14]1[CH2:18][C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)=[C:16]([CH3:26])[C@H:15]1[OH:27])=[O:13])[CH3:10].N1C=CN=C1>C(Cl)Cl>[CH2:9]([O:11][C:12]([C@@H:14]1[CH2:18][C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)=[C:16]([CH3:26])[C@H:15]1[O:27][Si:3]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 59627891HCID 59627891, compound

Product 1

HCID 67267363HCID 67267363, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylsilyl chloride (145 μL, 0.863 mmol, 1.5 equiv) was added dropwise to a solution of alcohol 88 (150 mg, 0.575 mmol) and imidazole (17 mg, 1.72 mmol, 3 equiv) in methylene chloride (4 ml) at 0° C. After stirring at 0° C. for 2 hr, the reaction was quenched with water (2.5 ml), and extracted with ethyl acetate (3×5 ml). The organic extracts were washed with brine (3.5 ml), and dried over anhydrous sodium sulfate. Filtration and evaporation of the solvents in vacuo furnished an oily crude product which was purified by flash column chromatography on silica (2-7% EtOAc/hexanes-) to give 93 (198 mg, 92%) as a yellow oil: [α]22D=−51.04 (c=0.7, CHCl3); TLC Rf=0.29 (silica gel, 25% EtOAc/hexanes); 1H NMR (600 MHz, CDCl3) δ 8.41 (s, 1H), 7.45-7.42 (dd, 1H, 3J=1.8 Hz, 2J=8.4 Hz), 7.2-7.18 (d, 1H, 3J=7.8 Hz), 5.12 (d, 1H, 3J=4.8 Hz), 4.2-4.16 (dd, 2H, 3J=7.2 Hz, 2J=14.4 Hz), 3.17-3.12 (m, 1H), 3.0-2.89 (m, 2H), 2.3 (s, 3H), 1.97 (s, 3H), 1.29-1.26 (t, 3H, 3J=14.4 Hz), 0.98-0.95 (t, 9H, 3J=7.8 Hz), 0.67-0.63 (q, 6H, 3J=7.8 Hz); 13C NMR (100 MHz, CDCl3) δ 175.31, 153.31, 149.87, 139.09, 136.51, 134.07, 131.15, 122.39, 84.53, 60.83, 51.58, 37.40, 18.42, 14.46, 13.31, 7.03, 5.15; HRMS calcd for C21H33NO3Si+H+376.2308; found 376.2302 [M+H+].

Workup

  1. customthe reaction was quenched with water (2.5 ml)
  2. extractionextracted with ethyl acetate (3×5 ml)
  3. washThe organic extracts were washed with brine (3.5 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration and evaporation of the solvents in vacuo
  6. customfurnished an oily crude product which
  7. customwas purified by flash column chromatography on silica (2-7% EtOAc/hexanes-)

Sources & evidence

ORD record
ord-5e58bfdd431c49eca60e79158df0ee50
Source dataset
uspto-grants-2011_02
Patent number
US07893268B2

Reaction notes

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