Hydrochloric Acid → Sodium 2-{3-[(4,6-diphenyl-2-pyridyl)oxy]propyloxy}acetate

HRID 2396509

반응식

HRID 2396509 반응식
CC([O-])(C)C.[K+].[C:7]1([C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]=[C:15]([O:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:31][C:32]([O-:34])=[O:33].[K+].Cl.[OH-].[Na+:38]>C(O)(C)(C)C.O.CC(C)=O>[C:7]1([C:13]2[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:16]=[C:15]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:31][C:32]([O-:34])=[O:33])[CH:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1.[Na+:38]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 189872833-[(4,6-Diphenyl-2-pyridyl)oxy]-1-propanolHCID 23665647Potassium tert-butoxideHCID 23681702HCID 23681702, 화합물

생성물 1

HCID 23712831Sodium 2-{3-[(4,6-diphenyl-2-pyridyl)oxy]propyloxy}acetate

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 6386tert-Butanol용매

반응 조건

온도
100 °C

실험 절차

To potassium tert-butylate (5.52 g) in tert-butanol (60 cc) heated to 100° C. is added, in the form of a homogeneous solid, a mixture of 3-[(4,6-diphenyl-2-pyridyl)oxy]-1-propanol (5 g) and potassium 2-bromoacetate (4.35 g). The addition is carried out in 1 hour. The reaction mixture is then heated for 48 hours at 100° C. and then poured in iced water (100 g). The pH of the aqueous phase is brought to 5 by addition of 1N hydrochloric acid. The mixture is then extracted with dichloromethane (3×50 cc) after saturating the aqueous phase with sodium chloride. The combined organic phases are dried over sodium sulphate and concentrated to dryness at 40° C. under reduced pressure. The oily residue obtained is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-diethyl ether 65-35 and then 40-60 and then diethyl ether-methanol;9-1). The white solid obtained, taken up in acetone (5 cc), is treated with sodium hydroxide pellets (0.19 g) and distilled water (1.cc). The mixture is stirred for 60 hours at room temperature. The precipitate obtained is filtered, washed with ethyl ether and dried at 40° C. under reduced pressure. (white solid; m.p.=285°-288° C.)

후처리

  1. additionis added, in the form of a homogeneous solid
  2. additionThe addition
  3. extractionThe mixture is then extracted with dichloromethane (3×50 cc)
  4. concentrationafter saturating the aqueous phase with sodium chloride
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated to dryness at 40° C. under reduced pressure
  7. customThe oily residue obtained
  8. customis purified by chromatography under pressure on silica gel (30-60 mm
  9. customThe white solid obtained
  10. distillationdistilled water (1.cc)
  11. customThe precipitate obtained
  12. filtrationis filtered
  13. washwashed with ethyl ether
  14. customdried at 40° C. under reduced pressure

출처 및 근거

ORD 기록
ord-2f37e26d51f3486fa84c21612d1d8c36
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05492915

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