Methanol → HCID 131729625, compound

HRID 1690724Notes

Reaction equation

HRID 1690724 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:33])([CH3:32])[C:8]1N=[CH:10][N:11](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[C:34]([C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[CH2:38]Br)#[N:35].C([NH:46]CC)C.CO>C(#N)C>[C:1]([SiH2:5][O:6][C:7]([CH3:33])([CH3:32])[C:8]1[N:35]([CH2:34][C:36]2[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=2[C:38]#[N:46])[CH:10]=[N:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8021DiethylamineHCID 895992-(Bromomethyl)benzonitrileHCID 131729626HCID 131729626, compound

Product 1

HCID 131729625HCID 131729625, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxymethyl)-1-trityl-1H-imidazole (11.1 g, 24.4 mmol) and 2-cyanobenzyl bromide (5.02 g, 25.62 mmol) in acetonitrile (100 mL) are heated to 60° C. overnight, whereupon diethylamine (30 mL) is added. After 30 min, methanol (2 mL) is added. After 30 min the volatiles are removed in vacuo. The residue is taken up in dichloromethane and washed with water. The organic layer is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel flash chromatography (elution with dichloromethane-methanol, 49:1) to yield partially purified 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-ylmethyl]-benzonitrile which is used in the next step without further purification; MS (ESI) m/z 328.2 (M+H).

Workup

  1. additionis added
  2. customAfter 30 min the volatiles are removed in vacuo
  3. washwashed with water
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel flash chromatography (elution with dichloromethane-methanol, 49:1)

Sources & evidence

ORD record
ord-9ae5361158a34ca0b19906401d6d6ffa
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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