Chloromethyl Methyl Ether → methyl 5-bromo-6-cyclohexyl-4-(methoxymethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008994

Reaktionsgleichung

Reaktionsgleichung von HRID 1008994
[Br:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[H-].[Na+].[CH3:22][O:23][CH2:24]Cl>CN(C=O)C>[Br:1][C:2]1[N:6]([CH2:22][O:23][CH3:24])[C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Produkt 1

HCID 67298629methyl 5-bromo-6-cyclohexyl-4-(methoxymethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (prepared as in Example 7, Step 1) was dissolved in DMF and sodium hydride (1.4 eq.) was added. The mixture was stirred at RT until evolution of gas had ceased, then chloromethyl methyl ether (excess) was added and stirring was continued. After 5 h all volatiles were evaporated i. vac. and the residual material was filtered through silica gel (PE:Et2O, 12:1). The product was obtained as a colourless solid (66%). 1H-NMR (400 MHz, CDCl3, 300 K, δ): 7.73 (s, 1H), 5.41 (s, 2H), 3.90 (s, 3H), 3.32 (s, 3H), 2.73-2.67 (m, 1H), 1.90-1.76 (m, 5H), 1.65-1.58 (m, 2H), 1.47-1.29 (m, 3H).

Aufarbeitung

  1. stirringstirring
  2. customAfter 5 h all volatiles were evaporated i
  3. filtrationand the residual material was filtered through silica gel (PE:Et2O, 12:1)

Quellen und Nachweise

ORD-Eintrag
ord-7e8277cacd9844d8b8c9787fe29a0c3e
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973026B2

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