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

HRID 1448720

반응식

HRID 1448720 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-82330359a3174551a5716949c44cf368
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04187243

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