Dimethyl Carbonate → HCID 21530394, compound
Reaction equation
[H-].[Na+].[S:3]1(=[O:16])(=[O:15])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[CH2:6][CH2:5][CH2:4]1.[CH3:17][O:18][C:19](=O)[O:20]C>O1CCCC1>[O:14]=[C:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:3](=[O:15])(=[O:16])[CH2:4][CH2:5][CH:6]1[C:19]([O:18][CH3:17])=[O:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a slurry of 0.3 mol of sodium hydride in 200 ml of tetrahydrofuran was added a solution of 21 g (0.1 mol) of 3,4-dihydro-1-benzothiepin-5(2H)-one 1,1-dioxide in 800 ml of tetrahydrofuran. The mixture was stirred at room temperature for 2 hours and a solution of 27 g (0.3 mol) of dimethylcarbonate in 50 ml of tetrahydrofuran was added. It was refluxed under a nitrogen atmosphere for 20 hours, part of the tetrahydrofuran was removed by distillation, the residue was carefully poured into ice water containing excess hydrochloric acid, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate, and evaporated to give 36 g of semi-solid which gave a positive ferric chloride test and an infrared band at 175° cm-1. It was used in subsequent reactions without further purification.
Workup
- temperatureIt was refluxed under a nitrogen atmosphere for 20 hours
- custompart of the tetrahydrofuran was removed by distillation
- additionthe residue was carefully poured into ice water containing excess hydrochloric acid
- extractionthe mixture was extracted with dichloromethane
- washThe organic layer was washed with water
- dry with materialdried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-70aa922353ca41f38a8447a91d124523
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03962261
Reaction notes
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