Water → (2-(4-(Trifluoromethyl)phenyl)thiazole-4,5-diyl)dimethanol

HRID 1766128노트

반응식

HRID 1766128 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:31])([F:30])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]([C:25](OCC)=[O:26])=[C:18]([C:20](OCC)=[O:21])[N:19]=2)=[CH:11][CH:10]=1.S(=O)(=O)(O)O.O>C1COCC1.C(OCC)(=O)C.ClCCl>[OH:26][CH2:25][C:17]1[S:16][C:15]([C:12]2[CH:11]=[CH:10][C:9]([C:8]([F:31])([F:30])[F:7])=[CH:14][CH:13]=2)=[N:19][C:18]=1[CH2:20][OH:21]

참가 물질

8

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 11975782Diethyl 2-(4-(trifluoromethyl)phenyl)thiazole-4,5-dicarboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 11974006(2-(4-(Trifluoromethyl)phenyl)thiazole-4,5-diyl)dimethanol

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매2회

실험 절차

To a suspension of lithium aluminum hydride (0.14 wt) in THF (3.4 vols), add a solution of the diethyl 2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-4,5-dicarboxylate (1.0 wt, 1.0 eq), dissolved in THF (2 vols) at a rate such that the temperature of the reaction mixture is maintained at below −10° C. The addition time is 1.5–3.0 hr. After the addition is complete, stir the reaction mixture at ambient temperature for 18 h. Quench the reaction by adding aqueous 16% sulfuric acid (2.4 vols). Charge ethyl acetate (5 vols) with stirring to the reaction mixture followed with water (5 vols). Filter the resulting two phase mixture through celite (0.4 wt). Separate the layers and wash the organic layer with water (4×4 vols) and with brine (2×4 vol). Reduce the total volume of the reaction mixture via vacuum distillation to leave the solid suspended in ethyl acetate (1–1.5 vols). Dilute the slurry with dichloromethane (5 vols) and stir the suspension for at least 6 h. Filter the tan-colored solid. Wash the wet cake with dichloromethane (2 vols) and dry the wet cake at 45° C. under mild vacuum to afford the title compound as an off-white solid.

후처리

  1. temperatureis maintained at below −10° C
  2. waitThe addition time is 1.5–3.0 hr
  3. additionAfter the addition
  4. customQuench
  5. customthe reaction
  6. filtrationFilter the resulting two phase mixture through celite (0.4 wt)
  7. customSeparate the layers
  8. washwash the organic layer with water (4×4 vols)
  9. distillationReduce the total volume of the reaction mixture via vacuum distillation
  10. customto leave the solid
  11. stirringstir the suspension for at least 6 h
  12. filtrationFilter the tan-colored solid
  13. washWash the wet cake with dichloromethane (2 vols)
  14. customdry the wet cake at 45° C. under mild vacuum

출처 및 근거

ORD 기록
ord-07373bc5f2544535bac1fb53a5c0567d
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07229998B2

반응 노트

불러오는 중…