Reaktion #1878208

Reaktionsgleichung

methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate

water

sodium hydrogenphosphate

methanol tetrahydrofuran

→

methyl 3-methylene-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate

Lösungsmittel

dichloromethane

—

1/1

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Filtrationfiltering off the mercury
3. 3
   Sonstigethe phases are separated
4. 4
   Extraktionthe aqueous phase is extracted 3 times with dichloromethane
5. 5
   WaschenThe combined organic phases are washed with a slightly acidic aqueous solution
6. 6
   SonstigeAfter drying
7. 7
   Einengenconcentrating under vacuum, 49 mg (98%) of methyl 3-methylene-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate
8. 8
   Sonstigeare obtained without additional purification in the form of an oil

Vorschrift

728 mg (0.95 mmol) of 3% sodium amalgam are added portionwise at 0° C. to a suspension of 85 mg (0.23 mmol) of methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to example 1, and of 116 mg (0.95 mmol) of sodium hydrogenphosphate in 10 ml of a 1/1 methanol/tetrahydrofuran binary mixture. The reaction medium is subsequently stirred at ambient temperature for 4 hours. After addition of water and dichloromethane and filtering off the mercury, the phases are separated and the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are washed with a slightly acidic aqueous solution and then with brine. After drying and then concentrating under vacuum, 49 mg (98%) of methyl 3-methylene-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate are obtained without additional purification in the form of an oil; 1H NMR (300 MHz, CDCl3): 2.53. (m, 2H), 2.93 (m, 2H), 3.89 (s, 3H), 4.49 (s, 2H), 5.0 (d, J=4.1 Hz, 2H), 7.0 (d, J=8.1 Hz, 1H), 7.86 (m, 2H).

Quelle