Carbon Dioxide → HCID 19428110, compound
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH:14]([CH2:17][C:18](OCC)=[O:19])[NH:13][C:12]=2[CH:23]=1.C(=O)=O.[OH-].[Na+]>O1CCCC1.O.CC(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH:14]([CH2:17][CH2:18][OH:19])[NH:13][C:12]=2[CH:23]=1Participants
Procedure
150 ml of tetrahydrofuran are placed in a 1 litre reactor which is cooled with a mixture of ice and salt, and, under an argon atmosphere, 5.92 g (0.156 mol) of lithium aluminium hydride are added, followed by dropwise addition of 23.52 g (0.0973 mol) of ethyl (±)-6-chloro-3,4-dihydro-2H-1,4-benzoxazine-3-acetate dissolved in 150 ml of tetrahydrofuran, and the mixture is stirred for 1.5 hours. The reactor is cooled with a mixture of cardice and acetone, 40 ml of water and 20 ml of 1N sodium hydroxide are added dropwise and the mixture is stirred for 0.5 hour. The precipitate is filtered on kieselgel and rinsed with tetrahydrofuran and then with ethyl acetate, and the solvent is evaporated off. 27.5 g of crude product are isolated, which product is purified by chromatography on a column of silica gel, eluting with a cyclohexane/ethyl acetate (1/1 ratio) mixture.
Workup
- temperaturewhich is cooled with a mixture of ice and salt
- additionare added dropwise
- stirringthe mixture is stirred for 0.5 hour
- filtrationThe precipitate is filtered on kieselgel
- washrinsed with tetrahydrofuran
- customwith ethyl acetate, and the solvent is evaporated off
Sources & evidence
- ORD record
- ord-54a06c85c5e64c6b99ba1e4a528dd7c2
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05550125
Reaction notes
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