Hydrochloric Acid → HCID 20150421, 화합물

HRID 568731노트

반응식

HRID 568731 반응식
[OH-].[K+].[OH:3][C:4]1[C:5]([CH3:22])=[C:6]([CH3:21])[C:7]2[O:12][C:11]([CH2:14][CH2:15][C:16]([OH:18])=O)([CH3:13])[CH2:10][CH2:9][C:8]=2[C:19]=1[CH3:20].S([O:28][CH3:29])(OC)(=O)=O.Cl.[CH3:31]N(C)C=O>C(O)C>[CH3:31][O:3][C:4]1[C:5]([CH3:22])=[C:6]([CH3:21])[C:7]2[O:12][C:11]([CH2:14][CH2:15][C:16]([O:28][CH3:29])=[O:18])([CH3:13])[CH2:10][CH2:9][C:8]=2[C:19]=1[CH3:20]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 9943542alpha-CEHC

생성물 1

HCID 20150421HCID 20150421, 화합물수율 53.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

An aqueous solution of potassium hydroxide (7.1 g in 10 ml of water) was added dropwise to a solution composed of 10 g (0.036 mol) of 3-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)propionic acid and 200 ml of ethanol in a nitrogen atmosphere and the mixture was stirred at room temperature for 30 minutes. The ethanol was distilled off from the reaction mixture under reduced pressure, toluene was added to the residue, and dehydration was effected azeotropically under reduced pressure. To the residue thus obtained, 200 ml of N,N-dimethylformamide was added for dissolution of the residue. To the solution was added dropwise, with vigorous stirring, 4.53 g (3.4 ml) of dimethyl sulfate while maintaining the solution at a temperature of room temperature to 50° C. After the addition, the reaction was conducted at 50° C. for 5 hours. After cooling to room temperature, the reaction mixture was poured into dilute hydrochloric acid and extracted with diethyl ether. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then filtered. Low-boiling substances were distilled off from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography to give 5.9 g (53.6% yield) of methyl 3-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)propionate

후처리

  1. distillationThe ethanol was distilled off from the reaction mixture under reduced pressure, toluene
  2. additionwas added to the residue, and dehydration
  3. customTo the residue thus obtained
  4. temperaturewhile maintaining the solution at a temperature of room temperature to 50° C
  5. additionAfter the addition
  6. waitthe reaction was conducted at 50° C. for 5 hours
  7. temperatureAfter cooling to room temperature
  8. extractionextracted with diethyl ether
  9. washThe extract was washed with water
  10. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. distillationLow-boiling substances were distilled off from the filtrate under reduced pressure
  13. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e992e99d331a4bf89afaeafa57d17f51
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04728650

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