Acetone Cyanohydrin → (4-Amino-chroman-7-yl)-acetonitrile

HRID 32092

반응식

HRID 32092 반응식
P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO[C:23](/[N:25]=N/C(OCC)=O)=O.[NH2:32][CH:33]1[C:42]2[C:37](=[CH:38][C:39]([CH2:43]O)=[CH:40][CH:41]=2)[O:36][CH2:35][CH2:34]1.CC(C)(O)C#N>C1COCC1>[NH2:32][CH:33]1[C:42]2[C:37](=[CH:38][C:39]([CH2:43][C:23]#[N:25])=[CH:40][CH:41]=2)[O:36][CH2:35][CH2:34]1

참가 물질

6

반응물 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 55294793(4-Aminochroman-7-yl)-methanol

생성물 1

HCID 68929026(4-Amino-chroman-7-yl)-acetonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-20 °C

실험 절차

To a 125 mL flame dry 3-neck round bottom flask was added P(Ph)3 (4.4 g, 16.74 mmol) and THF (50 mL). After cooling to −20° C., DEAD (3.3 mL, 16.74 mmol) was added dropwise via the addition funnel. After stirring for 20 min at −20° C., (4-aminochroman-7-yl)-methanol (2.0 g, 11.16 mmol) in THF (75 mL) was added dropwise via the addition funnel. It was stirred for another 30 min. acetone cyanohydrin (3.1 mL, 33.48 mmol) was then added dropwise via the addition funnel. The resulting mixture was warmed to RT and stirred for 18 h. Solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH mixture (95:5) gave final compound. MS m/z: 189.12 (M+H). Calc'd. for C11H12N2O-188.23.

후처리

  1. temperatureTo a 125 mL flame
  2. customdry 3-neck round bottom flask
  3. additionwas then added dropwise via the addition funnel
  4. temperatureThe resulting mixture was warmed to RT
  5. stirringstirred for 18 h
  6. customSolvent was evaporated in vacuo
  7. customThe residue was purified by chromatography on silica gel
  8. washElution with CH2Cl2

출처 및 근거

ORD 기록
ord-75786cefe3514f76a38afa3a8f3808ad
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425631B2

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