tert-Butanol → 1-(6-(2,2,2-Trifluoroethoxy)pyridin-3-yl)ethane-1,2-diol

HRID 623476노트

반응식

HRID 623476 반응식
[C:1]([OH:5])(C)([CH3:3])[CH3:2].CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:27]C)C=C4)N(CC2)C1.[F:64][C:65]([F:77])([F:76])[CH2:66][O:67][C:68]1[CH:73]=[CH:72]C(C=C)=[CH:70][N:69]=1>O>[F:64][C:65]([F:77])([F:76])[CH2:66][O:67][C:68]1[N:69]=[CH:70][C:2]([CH:1]([OH:5])[CH2:3][OH:27])=[CH:72][CH:73]=1

참가 물질

5

반응물 3

HCID 6386tert-ButanolHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 675114252-(2,2,2-Trifluoroethoxy)-5-vinylpyridine

생성물 1

HCID 675099191-(6-(2,2,2-Trifluoroethoxy)pyridin-3-yl)ethane-1,2-diol수율 86%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 200 mL flask is charged with tert-butanol (30 mL), water (30 mL) and AD-mix-beta (10 g, 4.92 mmol). Stirring room temperature producted two clear phased. The lower aquerous phase bright yellow. The mixture is cooled to 0° C. Whereupon some of the dissolved salts precipitate. 2-(2,2,2-trifluoroethoxy)-5-vinylpyridine (1.00 g, 4.92 mmol, Step-2) is added at once, and the heterogeneous slurry is stirred vigorously at 0° C. for 15 hours. White precipitate is filtrated and filtrate is removed under reduced pressure. The residue is extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:3) to give 1.01 g (86% yield) of the title compound as colorless oil.

후처리

  1. temperatureThe mixture is cooled to 0° C
  2. stirringis stirred vigorously at 0° C. for 15 hours
  3. filtrationWhite precipitate is filtrated
  4. customfiltrate is removed under reduced pressure
  5. extractionThe residue is extracted with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:3)

출처 및 근거

ORD 기록
ord-2abfa2837b004f299251ad775594e269
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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