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

HRID 32092

Reaction equation

HRID 32092 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-75786cefe3514f76a38afa3a8f3808ad
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Linked notes

Loading…