Hydrochloric Acid → 5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 870316

반응식

HRID 870316 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=O.[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1.C(OC(C)C)(=O)C.Cl>CCCCCCC.O.O1CCCC1>[OH:13][C:11](=[C:19]1[C:20](=[O:21])[O:22][C:15]([CH3:23])([CH3:14])[O:16][C:17]1=[O:18])[CH2:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[F:1]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7915Isopropyl Acetate2회HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27779502,4,5-Trifluorophenylacetic acid

생성물 1

HCID 547114775-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione수율 60.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8900Heptane용매

반응 조건

온도
30 °C

실험 절차

2,4,5-trifluorophenylacetic acid (30 g), tetrahydrofuran (360 mL), 1,1-carbonyl diimidazole (25.5 g) at about 50° C., and meldrums acid (22.7 g) are combined. The mixture is stirred for about five hours at the same temperature. The reaction mass is then cooled to about 30° C. Isopropyl acetate (180 mL) and water (180 mL) are added and stirred for about 30 minutes. The reaction mass is cooled to about 0° C. and pH is adjusted to about 2.4 using 36% aqueous hydrochloric acid. The organic layer is separated, washed with 0.1 N aqueous hydrochloric acid and distilled off completely. To the residue obtained, n-heptane (140 mL) and isopropyl acetate (70 mL) are charged at about 30° C. and stirred at about 0° C. for about 90 minutes. The separated solid is filtered and washed with a mixture of n-heptane (20 mL) and isopropyl acetate (10 mL). The wet cake is dried at about 50° C. for about 4 hours to afford the title compound. (Yield: 60.1%; purity by HPLC: 98.0%)

후처리

  1. customat about 50° C.
  2. stirringstirred for about 30 minutes
  3. temperatureThe reaction mass is cooled to about 0° C.
  4. customThe organic layer is separated
  5. washwashed with 0.1 N aqueous hydrochloric acid
  6. distillationdistilled off completely
  7. customTo the residue obtained
  8. stirringstirred at about 0° C. for about 90 minutes
  9. filtrationThe separated solid is filtered
  10. washwashed with a mixture of n-heptane (20 mL) and isopropyl acetate (10 mL)
  11. customThe wet cake is dried at about 50° C. for about 4 hours

출처 및 근거

ORD 기록
ord-fd26ab66b9a54b03a57a1da72ec4fac0
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969558B2

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