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

HRID 1779375ノート

反応式

HRID 1779375 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-76dbd0cc59574a2693beb94c3f6559bc
出典データセット
uspto-grants-1997_05
特許番号
US05627189

反応ノート

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