反応 #60370

反応方程式

acetone cyanohydrin

(4-aminochroman-7-yl)-methanol

P(Ph)3

DEAD

→

final compound

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

溶媒

THF

THF

反応条件

後処理

1. 1
   温度To a 125 mL flame
2. 2
   その他dry 3-neck round bottom flask
3. 3
   workup.ADDITIONwas then added dropwise via the addition funnel
4. 4
   温度The resulting mixture was warmed to RT
5. 5
   workup.STIRRINGstirred for 18 h
6. 6
   その他Solvent was evaporated in vacuo
7. 7
   その他The residue was purified by chromatography on silica gel
8. 8
   洗浄Elution with CH2Cl2

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.

出典