Hydrochloric Acid → 1-(4,4-Dimethylthiochroman-6-yl)ethanone

HRID 6534

반응식

HRID 6534 반응식
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1.[C:13](Cl)(=[O:15])[CH3:14].O.Cl>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[CH:10]=2)[S:5][CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6367Acetyl chlorideHCID 110194304,4-Dimethylthiochroman2회

생성물 1

HCID 117083551-(4,4-Dimethylthiochroman-6-yl)ethanone

시약·촉매·용매 1

HCID 241Benzene용매

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).

후처리

  1. temperatureheated
  2. temperatureat reflux for 0.5 hours
  3. temperatureAfter being cooled to room temperature
  4. customthe organic layer was separated
  5. extractionthe aqueous layer extracted with 5×50 ml benzene
  6. washwashed with 5% sodium carbonate, water, saturated NaCl
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customthe residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes)
  10. distillationfollowed by kugelrohr distillation (150 degrees C., 0.7 mm)

출처 및 근거

ORD 기록
ord-96350377ef0540789eec3b3c750eb3d6
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248777

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