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

HRID 32092

反応式

HRID 32092 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-75786cefe3514f76a38afa3a8f3808ad
出典データセット
uspto-grants-2008_09
特許番号
US07425631B2

関連ノート

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