Dimethylformamide → 2-(2-Cyanoethylidene)-bicyclo[2.2.1]heptane

HRID 1448720

反応式

HRID 1448720 の反応式
[CH:1]([CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH2:5][CH2:6]2)=O.[C:10]([CH2:12]C(O)=O)#[N:11].[OH-].[NH4+].CN(C)C=O>C1C=CC=CC=1>[C:10]([CH2:12][CH:1]=[C:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH2:5][CH2:6]2)#[N:11]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 14923Ammonium HydroxideHCID 86864Bicyclo[2.2.1]heptane-2-carbaldehyde

生成物 1

HCID 544239752-(2-Cyanoethylidene)-bicyclo[2.2.1]heptane収率 79%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A stirred solution of 95 g (0.77 mol) of 2-formylbicyclo[2.2.1]heptane, 65 g (0.76 mol) of cyanoacetic acid, 2 ml of ammonium hydroxide (58%), 132 ml of dimethylformamide, and 170 ml benzene was heated to reflux and the water removed with a Dean-Stark trap. The reaction was allowed to continue until the evolution of carbon dioxide ceased (approx. 24 hrs.). Upon completion, the reaction was cooled and the solvent removed under reduced pressure. The residual oil was distilled under vacuum to give 88 g (79% yield) of 2-(2-cyanoethylidene)-bicyclo[2.2.1]heptane: b.p. 72°-80° C./1 mm; ir 2960, 2870, 2260, 1685, 1450, 1420, 1305, 920; nmr 1.15-2.8 (10H, m), 2.96 (2H, m), 4.9-5.4 (1H, m); ms 147.

後処理

  1. temperatureto reflux
  2. customthe water removed with a Dean-Stark trap
  3. custom(approx. 24 hrs.)
  4. temperatureUpon completion, the reaction was cooled
  5. customthe solvent removed under reduced pressure
  6. distillationThe residual oil was distilled under vacuum

出典と根拠

ORDレコード
ord-82330359a3174551a5716949c44cf368
出典データセット
uspto-grants-1980_02
特許番号
US04187243

関連ノート

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