Imidazole → HCID 14652367, compound

HRID 2352506Notes

Reaction equation

HRID 2352506 reaction equation
[OH:1][C:2]([CH:13]1[S:18][CH2:17][CH2:16][CH2:15][S:14]1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][C:5]#[CH:6].N1C=CN=C1.Cl[Si:25]([CH3:28])([CH3:27])[CH3:26].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:7]1([C:2]([CH:13]2[S:14][CH2:15][CH2:16][CH2:17][S:18]2)([O:1][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3][CH2:4][C:5]#[CH:6])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 11430Potassium CarbonateHCID 14652366HCID 14652366, compound

Product 1

HCID 14652367HCID 14652367, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(1-Hydroxy-1-phenylpent-4-ynyl)-1,3 -dithiane (1.7 g 6.1 mmol) and 1.2 g (15 mmol) of imidazole was stirred in 25 mL of methylene chloride and 0.9 mL (15 mmol) of chlorotrimethylsilane was added. The mixture was stirred overnight when it was poured onto 20 mL of 10% aqueous K2CO3. The organics were washed with brine, dried (Na2SO4) and concentrated at reduced pressure. The residue was mixed with Celite and chromatographed on 110 g of silica (99:1, hexane:ethyl acetate, then 2% ethyl acetate) to give 2.14 g (90%) of a product that crystallized upon concentration at reduced pressure. Analytical TLC (silica, 9:2, hexane:ethyl acetate) Rf0.56; 1H NMR (CDCl3) δ1.65-2.05 (m, 5H), 2.05-2.2 (m, 1H), 2.28-2.4 (m, 1H), 2.45-2.6 (m, 1H), 2.7-2.87 (m, 4H), 4.37 (s, 1H), 7.25-7.4 (m, 3H), 7.42-7.5 (m, 2H).

Workup

  1. washThe organics were washed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated at reduced pressure
  4. additionThe residue was mixed with Celite
  5. customchromatographed on 110 g of silica (99:1, hexane

Sources & evidence

ORD record
ord-217688445b2b407583378886909ed165
Source dataset
uspto-grants-1989_10
Patent number
US04877779

Reaction notes

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