Diisopropylethylamine → 2-((Methoxy)(4-phenoxyphenyl)methylene)malononitrile

HRID 403472ノート

反応式

HRID 403472 の反応式
[C:1]([C:3]([C:19]#[N:20])=[C:4]([OH:18])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)#[N:2].[CH:21](N(C(C)C)CC)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C.CO.C1COCC1>[C:1]([C:3]([C:19]#[N:20])=[C:4]([O:18][CH3:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)#[N:2]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 223471552-(Hydroxy-(4-phenoxyphenyl)methylene)propanedinitrile

生成物 1

HCID 223472272-((Methoxy)(4-phenoxyphenyl)methylene)malononitrile

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

1,1-Dicyano-2-hydroxy-2-(4-phenoxyphenyl)ethene (56.5 g) in acetonitrile (780 mL) and methanol (85 mL) is stirred under nitrogen at 0° C. while adding diisopropylethylamine (52.5 mL) followed by 2M trimethylsilyldiazomethane (150 mL) in THF. The reaction is stirred for 2 days at 20° C., and then 2 g of silica is added (for chromatography). The brown-red solution is evaporated in vacuo, the residue dissolved in ethyl acetate and washed well with water then brine, dried and evaporated. The residue is extracted with diethyl ether (3×250 mL), decanting from insoluble oil. Evaporation of the ether extracts gives 22.5 g of 1,1-dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene as a pale orange solid. The insoluble oil is purified by flash chromatography to give 15.0 g of a red-orange oil.

後処理

  1. addition2 g of silica is added (for chromatography)
  2. customThe brown-red solution is evaporated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed well with water
  5. dry with materialbrine, dried
  6. customevaporated
  7. extractionThe residue is extracted with diethyl ether (3×250 mL)
  8. customdecanting from insoluble oil
  9. customEvaporation of the ether

出典と根拠

ORDレコード
ord-1dbd4906e1f747f1b8a8eab18359b5e8
出典データセット
uspto-grants-2014_06
特許番号
US08748438B2

反応ノート

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