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

HRID 32092

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: -20 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-75786cefe3514f76a38afa3a8f3808ad
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07425631B2

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