반응 #6630

반응 방정식

4,4-dimethylthiochroman

Compound 61

4,4-dimethylthiochroman

acetyl chloride

water

hydrogen chloride

→

title compound

4,4-Dimethyl-6-acetylthiochroman

용매

benzene

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도at reflux for 0.5 hours
3. 3
   온도After being cooled to room temperature
4. 4
   기타the organic layer was separated
5. 5
   추출the aqueous layer extracted with 5×50 ml benzene
6. 6
   세척washed with 5% sodium carbonate, water, saturated NaCl
7. 7
   건조dried (MgSO4)
8. 8
   기타The solvent was removed in vacuo
9. 9
   기타the residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes)
10. 10
    workup.DISTILLATIONfollowed by kugelrohr distillation (150 degrees C., 0.7 mm)

실험 절차

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).

출처