Acetic Acid → 3-(8-Acetoxy-9-bromononyl)-1-methylthymine

HRID 361524ノート

反応式

HRID 361524 の反応式
[OH:1][CH:2]([CH2:20]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19].[BrH:22].[C:23]([OH:26])(=O)[CH3:24].C(=O)(O)[O-].[Na+]>ClCCl>[C:23]([O:1][CH:2]([CH2:20][Br:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19])(=[O:26])[CH3:24]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 232879543-(8,9-Dihydroxynonyl)-1-methylthymine

生成物 1

HCID 232959773-(8-Acetoxy-9-bromononyl)-1-methylthymine収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-(8,9-dihydroxynonyl)-1-methylthymine (2.16 g, 7.6 mmol) and a 30% solution of hydrogen bromide in acetic acid (4.5 mL, 23 mmol ) was stirred for 1 hour. The reaction was added slowly to a beaker containing sodium bicarbonate (8.4 g, 0.1 mol), ice water (30 mL), and dichloromethane (30 mL). The layers were separated and the aqueous layer extracted with dichloromethane (2×60 mL). The combined organic layers were washed with water (30 mL), saturated aqueous salt solution (30 mL), and dried over sodium sulfate. The solvent was removed to yield 2.59 g (85% yield) 3-(8-acetoxy-9-bromononyl)-1-methylthymine (inventive compound no. 1908) as a thick, slightly orange oil.

後処理

  1. additionThe reaction was added slowly to a beaker
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (2×60 mL)
  4. washThe combined organic layers were washed with water (30 mL), saturated aqueous salt solution (30 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed

出典と根拠

ORDレコード
ord-abb7c4eaed674d7a955ff2c48421db1a
出典データセット
uspto-grants-1999_02
特許番号
US05866576

反応ノート

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