tert-Butanol → 2,2-DIMETHYLTETRAHYDRO-2H-PYRAN-4-CARBONITRILE

HRID 2088959Notes

Reaction equation

HRID 2088959 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.C(O)(C)(C)C.[CH3:19][C:20]1([CH3:27])[CH2:25][C:24](=O)[CH2:23][CH2:22][O:21]1.CC(C)([O-])C.[K+]>C(COC)OC.C(OCC)C>[CH3:19][C:20]1([CH3:27])[CH2:25][CH:24]([C:10]#[N:11])[CH2:23][CH2:22][O:21]1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 161915Tosylmethyl isocyanideHCID 17381592,2-Dimethyltetrahydropyran-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 122964252,2-DIMETHYLTETRAHYDRO-2H-PYRAN-4-CARBONITRILEYield 84.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-20 °C

Procedure

p-Toluenesulfonylmethyl isocyanide (693 mg) and tert-butanol (438 μl) were added to a solution of 2,2-dimethyltetrahydro-4H-pyran-4-one (350 mg) in dimethoxyethane (10 ml) with stirring. Potassium tert-butoxide (766 mg) were added in three portions under cooling at −20° C. The mixture was heated to room temperature and then stirred for 18 hours. Diethyl ether was added and the mixture was filtered through Celite. Thereafter, the solvent was evaporated under reduced pressure to give the title compound (321 mg).

Workup

  1. temperatureThe mixture was heated to room temperature
  2. stirringstirred for 18 hours
  3. filtrationthe mixture was filtered through Celite
  4. customThereafter, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-275f141250b7490c9e50328f6eb7b12b
Source dataset
uspto-grants-2013_05
Patent number
US08436012B2

Reaction notes

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