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

HRID 361524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 361524
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-abb7c4eaed674d7a955ff2c48421db1a
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

Notizen zur Reaktion

Wird geladen…