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

HRID 404869ノート

反応式

HRID 404869 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e1b134c4ec7948afa5c0028a2a40379c
出典データセット
uspto-grants-2014_06
特許番号
US08748627B2

反応ノート

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