Acetic Acid → 3-(5-Acetoxy-6-bromohexyl)-1-methyluracil

HRID 399757ノート

反応式

HRID 399757 の反応式
[OH:1][CH:2]([CH2:16]O)[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([CH3:14])[C:8]1=[O:15].[BrH:18].[C:19]([OH:22])(=O)[CH3:20].C(=O)(O)[O-].[Na+]>ClCCl.O>[C:19]([O:1][CH:2]([CH2:16][Br:18])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([CH3:14])[C:8]1=[O:15])(=[O:22])[CH3:20]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 232879503-(5,6-Dihydroxyhexyl)-1-methyluracil

生成物 1

HCID 232959163-(5-Acetoxy-6-bromohexyl)-1-methyluracil収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

3-(5,6-Dihydroxyhexyl)-1-methyluracil (350 mg, 1.4 mmol) was stirred with 30% hydrogen bromide in acetic acid (0.87 ml, 4.3 mmol) for 45 minutes. The solution was added to a mixture of sodium bicarbonate (1.6 g), water (10 ml) and dichloromethane (20 ml). After 15 minutes of vigorous stirring, the layers were separated and the aqueous layer was extracted with dichloromethane (3×40 ml). The combined organic layers were dried over sodium sulfate and the solvent was evaporated under vacuum to give 3-(5-acetoxy-6-bromohexyl)-1-methyluracil (500 mg, 100% yield). The bromoacetate thus obtained was used in the next step without further purification. 3-(5-Acetoxy-6-bromohexyl)-1-methyluracil (360 mg, 1.0 mmol) was dissolved in methanol (5 ml) and treated with a solution of 1M sodium methoxide in methanol (1 ml). After stirring for 15 minutes, the solution was poured into water (10 ml) and extracted with dichloromethane (3×30 ml). The combined organic layers were dried over sodium sulfate and the solvents were evaporated to give 3-(5,6-oxidohexyl)-1-methyluracil (150 mg, 67% yield) as a colorless, oil.

後処理

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (3×40 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customthe solvent was evaporated under vacuum

出典と根拠

ORDレコード
ord-28b1200b787049f39798444d90da4d7f
出典データセット
uspto-grants-1998_10
特許番号
US05824677

反応ノート

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