Aluminium lithium hydride → 2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol

HRID 253205

반응식

HRID 253205 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:15][C:16]=1[CH3:17])C>C1COCC1>[OH:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:15][C:16]=1[CH3:17]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 57986743[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]acetic acid ethyl ester

생성물 1

HCID 226474902-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol수율 72%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
5 °C

실험 절차

Cool (0° C.) a solution of lithium aluminum hydride (5.3 mL, IM in THF) and add a solution of [5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester (Example 1, 1.4 g, 4.25 mmol) in THF (15 mL). On complete addition, remove the cold bath and stir for 2 hrs. Cool this solution to 5° C., and then add water (0.2 mL), dropwise, followed by NaOH solution (0.2 mL, 5M in water) and water (0.2 mL). Dilute the resulting mixture with ethyl acetate and then filter through a pad of celite. Wash the solids with dichloromethane and then concentrate the combined filtrates under reduced pressure. Purify the residue by flash chromatography (elute with 30% ethyl acetate 40% dichloromethane in heptane) to give the title compound as a yellow solid (0.879 g) Use the compound of Example 1 as the starting material to obtain the title compound.

후처리

  1. additionOn complete addition
  2. customremove the cold bath
  3. additionDilute the resulting mixture with ethyl acetate
  4. filtrationfilter through a pad of celite
  5. washWash the solids with dichloromethane
  6. concentrationconcentrate the combined filtrates under reduced pressure
  7. customPurify the residue
  8. washby flash chromatography (elute with 30% ethyl acetate 40% dichloromethane in heptane)

출처 및 근거

ORD 기록
ord-ab20c3bdc8af44b5afd89ae4774a77fb
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872032B2

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