Diazald → 1-Methoxy-2-cyano-6-phenyl-1-hexene

HRID 1779375Notes

Reaction equation

HRID 1779375 reaction equation
[OH-].[K+].[N+](=[CH2:5])=[N-].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[C:20]([C:22]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:23][OH:24])#[N:21]>O.C(OCC)C.C(O)C>[CH3:5][O:24][CH:23]=[C:22]([C:20]#[N:21])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 6628DiazaldHCID 9550Diazomethane4×HCID 14797Potassium HydroxideHCID 677216482-Cyano-6-phenyl-1-hexen-1-ol

Product 1

HCID 541732801-Methoxy-2-cyano-6-phenyl-1-hexene

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3.0 grams of potassium hydroxide in 6 mL of water was placed in a commercially available diazomethane generator. Ethanol, 8 mL, was added to the generator, and the contents of the generator were slowly warmed to 60° C. to 70° C. To this was added dropwise a solution of 4.6 grams (0.021 mole) of Diazald® in a minimum amount of diethyl ether. The diazomethane generated was condensed on a cold finger and, in turn, was allowed to drip into a stirred, cooled, solution of 2.5 grams (0.012 mole) of 2-cyano-6-phenyl-1-hexen-1-ol in a minimum of diethyl ether. The complete generation of diazomethane required about 30 to 45 minutes. Upon completion of the diazomethane generation, the reaction mixture was allowed to warm to ambient temperature. After this time the reaction mixture was concentrated under reduced pressure, yielding 2.4 grams of 1-methoxy-2-cyano-6-phenyl-1-hexene. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturethe contents of the generator were slowly warmed to 60° C. to 70° C
  2. customcondensed on a cold finger
  3. temperaturecooled
  4. customabout 30 to 45 minutes
  5. concentrationAfter this time the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-76dbd0cc59574a2693beb94c3f6559bc
Source dataset
uspto-grants-1997_05
Patent number
US05627189

Reaction notes

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