Sodium Hydroxide → (1-trityl-1H-1,2,4-triazol-3-yl)methanol

HRID 720611ノート

反応式

HRID 720611 の反応式
C[O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.C(OCC)(=O)C.O>[C:10]([N:7]1[CH:8]=[N:9][C:5]([CH2:3][OH:2])=[N:6]1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 58739241methyl 1-trityl-1H-1,2,4-triazole-3-carboxylate

生成物 1

HCID 13471694(1-trityl-1H-1,2,4-triazol-3-yl)methanol収率 51%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A solution of 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester (4.7 g, 0.12 mol) in tetrahydrofuran was added dropwise to a suspension of lithium aluminum hydride (724 mg, 0.12 mol) in tetrahydrofuran (63 mL) cooled to 0° C. The reaction mixture was allowed to gradually warm to 25° C. The reaction was then stirred at 25° C. for 48 h. At this time, the reaction was cooled to 0° C. and diluted with ethyl acetate (140 mL). The reaction mixture was then consecutively treated with water (0.925 mL), a 15% aqueous sodium hydroxide solution (0.925 mL), and water (2.8 mL). This mixture was stirred at 0° C. for 15 min. At this time, magnesium sulfate was added. The resulting mixture was filtered to remove the solids. The solids were washed with tetrahydrofuran and dichloromethane. The filtrate was concentrated in vacuo to afford (1-trityl-1H-[1,2,4]triazol-3-yl)-methanol (2.2 g, 51%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ 8.02 (s, 1H), 7.37 (m, 9H), 7.04 (m, 6H), 5.30 (broad s, 1H), 4.41 (s, 2H).

後処理

  1. temperatureto gradually warm to 25° C
  2. temperatureAt this time, the reaction was cooled to 0° C.
  3. stirringThis mixture was stirred at 0° C. for 15 min
  4. filtrationThe resulting mixture was filtered
  5. customto remove the solids
  6. washThe solids were washed with tetrahydrofuran and dichloromethane
  7. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-ed01bfc465b5449f917672a66670d628
出典データセット
uspto-grants-2006_11
特許番号
US07135475B2

反応ノート

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