Hydroxyamine hydrochloride → 4-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile

HRID 490393Notes

Reaction equation

HRID 490393 reaction equation
Cl.NO.[C:4]([SiH2:8][O:9][C:10]([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:11]1[CH:12]=[C:13]([CH:17]=O)[O:14][C:15]=1[CH3:16])([CH3:7])([CH3:6])[CH3:5].CC1OC=CC=1CCO.[Cl-].ClC1N(C)C=C[N+:43]=1C>ClCCl.O.C(N(CC)CC)C>[C:4]([SiH2:8][O:9][C:10]([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:11]1[CH:12]=[C:13]([C:17]#[N:43])[O:14][C:15]=1[CH3:16])([CH3:7])([CH3:6])[CH3:5]

Participants

8

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chlorideHCID 184446362-(2-Methylfuran-3-yl)ethan-1-olHCID 1317274384-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbaldehyde

Product 1

HCID 1317274374-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

Hydroxylamine hydrochloride (1.11 g, 16.0 mmoles) and triethylamine (2.22 ml) were added to a solution of 4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbaldehyde from (i)(6.3 g, 16.0 mmoles) in dichloromethane (125 ml) and the mixture was stirred at room temperature for 17 hours. After cooling to 0° C., 2-Chloro-1,3-dimethylimidazolium chloride (2.81 g, 16.6 mmoles) and triethylamine (4.6 ml) were added and the yellow suspension was stirred at room temperature for 24 hours. The mixture was diluted with water and extracted with dichloromethane. The combined extracts were washed with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and water, and finally dried (MgSO4). The solvent was evaporated and the residue was purified by flash chromatography (silica, cyclohexane/diethyl ether 99:1 v/v as eluent) to afford 4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile as a viscous oil, (3.75 g).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringthe yellow suspension was stirred at room temperature for 24 hours
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and water
  5. dry with materialfinally dried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was purified by flash chromatography (silica, cyclohexane/diethyl ether 99:1 v/v as eluent)

Sources & evidence

ORD record
ord-658a3ba5fb3b4b63926eda0b5bc9e684
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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