Acetic Anhydride → Acetate

HRID 1157851ノート

反応式

HRID 1157851 の反応式
[OH:1][CH2:2][C:3]1[N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([CH2:8][OH:9])=[CH:6][N:7]=1.C(N(CC)CC)C.[C:24]([O:27]C(=O)C)(=[O:26])[CH3:25]>ClCCl>[CH3:25][C:24]([O-:27])=[O:26].[C:24]([O:1][CH2:2][C:3]1[N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([CH2:8][OH:9])=[CH:6][N:7]=1)(=[O:26])[CH3:25]

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 143167542,5-bis-(hydroxymethyl)-N-benzylimidazole

生成物 2

HCID 175AcetateHCID 686179892-acetoxymethyl-5-hydroxymethyl-N-benzylimidazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2,5-bis-(hydroxymethyl)-N-benzylimidazole (436 mg, 2.0 mmol) in dichloromethane (10 mL) was added triethylamine (0.35 mL, 2.0 mmol) and acetic anhydride (0.19 mL, 2.0 mmol). The mixture was then stirred overnight (16 h) at room temperature. The reaction was then washed with aqueous ammonium chloride and the layers separated. The aqueous layer was extracted twice with dichloromethane. The combined organic fractions were then dried over anhydrous sodium sulfate and concentrated. Purification by chromatography on silica gel (5% methanol in dichloromethane) gave the monoacetate, 2-acetoxymethyl-5-hydroxymethyl-N-benzylimidazole, as a white powder (300 mg, 58%). 1H NMR (CDCl3) δ 1.83 (s, 3H), 4.49 (s, 2H), 5.06 (s, 2H), 5.33 (s, 2H), 6.97 (m, 2H), 7.28 (m, 3H).

後処理

  1. washThe reaction was then washed with aqueous ammonium chloride
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted twice with dichloromethane
  4. dry with materialThe combined organic fractions were then dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel (5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-4c45b45cfde047e9b4e95587b56a78ab
出典データセット
uspto-grants-2010_10
特許番号
US07807694B2

反応ノート

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