Methanol → 1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanol

HRID 404869노트

반응식

HRID 404869 반응식
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([C:20](=[O:22])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].CO.[BH4-].[Na+]>O1CCCC1>[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([OH:22])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 694364601-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanone

생성물 1

HCID 694373051-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanol수율 98.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Example 3A (320 mg, 0.89 mmol) in a mixture of 1:1 methanol:tetrahydrofuran (40 mL) was added sodium borohydride (67.5 mg, 1.78 mmol) and stirred at room temperature for 2.5 hours. The reaction mixture was quenched with acetone, the solvent removed in vacuum and the residue dissolved in dichloromethane. The organic phase was washed with water and brine, dried over magnesium sulfate filtered and evaporated, to produce the title compound (317 mg). 1H NMR (300 MHz, CDCl3) δ ppm 7.15-7.29 (m, 3H) 6.82-6.97 (m, 4H) 502-5.16 (m, 1H) 4.43-4.61 (heptet, J=6.25 Hz, 1H) 1.60 (d, J=6.62 Hz, 3H) 1.35 (d, J=6.25 Hz, 6H). MS (DCI): m/z 362 (M+H).

후처리

  1. customThe reaction mixture was quenched with acetone
  2. customthe solvent removed in vacuum
  3. dissolutionthe residue dissolved in dichloromethane
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-e1b134c4ec7948afa5c0028a2a40379c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748627B2

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