تفاعل #6630

معادلة التفاعل

4,4-dimethylthiochroman

Compound 61

4,4-dimethylthiochroman

acetyl chloride

water

hydrogen chloride

→

title compound

4,4-Dimethyl-6-acetylthiochroman

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةat reflux for 0.5 hours
3. 3
   درجة الحرارةAfter being cooled to room temperature
4. 4
   أخرىthe organic layer was separated
5. 5
   استخلاصthe aqueous layer extracted with 5×50 ml benzene
6. 6
   غسيلwashed with 5% sodium carbonate, water, saturated NaCl
7. 7
   تجفيفdried (MgSO4)
8. 8
   أخرىThe solvent was removed in vacuo
9. 9
   أخرىthe residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes)
10. 10
    workup.DISTILLATIONfollowed by kugelrohr distillation (150 degrees C., 0.7 mm)

الإجراء التجريبي

A solution of 14.3g (80.21 mmol) of 4,4-dimethylthiochroman (Compound 61) and 6.76g (86.12 mmol) of acetyl chloride in 65 ml benzene was cooled in an ice bath and treated dropwise with 26.712g (102.54 mmol) of stannic chloride. The mixture was stirred at room temperature for 12 hours, then treated with 65 ml water and 33 ml conc. hydrogen chloride and heated at reflux for 0.5 hours. After being cooled to room temperature, the organic layer was separated and the aqueous layer extracted with 5×50 ml benzene. The recovered organic fractions were combined and washed with 5% sodium carbonate, water, saturated NaCl and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes) followed by kugelrohr distillation (150 degrees C., 0.7 mm) to give the title compound as a pale yellow oil. PMR (CDCl3) & 1.35 (6H, s), 1.92-1.98 (2H, m) 2.54 (3H, s), 3.02-3.08 (2H, m), 7.13 (1H, d, J~8.6 Hz), 7.58 (1H, dd, J~8.6 Hz, Hz), 7.99 (1H, d, J~2Hz).

المصدر