반응 #60370

반응 방정식

acetone cyanohydrin

(4-aminochroman-7-yl)-methanol

P(Ph)3

DEAD

→

final compound

(4-amino-chroman-7-yl)-acetonitrile

용매

THF

THF

반응 조건

후처리

1. 1
   온도To a 125 mL flame
2. 2
   기타dry 3-neck round bottom flask
3. 3
   workup.ADDITIONwas then added dropwise via the addition funnel
4. 4
   온도The resulting mixture was warmed to RT
5. 5
   workup.STIRRINGstirred for 18 h
6. 6
   기타Solvent was evaporated in vacuo
7. 7
   기타The residue was purified by chromatography on silica gel
8. 8
   세척Elution with CH2Cl2

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.

출처