Sodium Chloride → HCID 12014811, compound
Reaction equation
[CH2:1]([C:4]([CH2:13][C:14]#[CH:15])(C(OC)=O)[C:5]([O:7][CH3:8])=[O:6])[C:2]#[CH:3].[Cl-].[Na+]>CS(C)=O.O.COC(C)(C)C>[CH2:1]([CH:4]([CH2:13][C:14]#[CH:15])[C:5]([O:7][CH3:8])=[O:6])[C:2]#[CH:3]Participants
6
Procedure
Dimethyl 2,2-di(2-propynyl)malonate (71 g) was treated to a Krapcho decarboxylation by heating at 170° C. with with sodium chloride (25 g) and water (23 ml) in dimethylsulfoxide (341 ml). After 15 hr, the solution was cooled and diluted with water and t-butyl methyl ether and extacted. The organic layer was washed with water (4×), brine, and then dried over sodium sulfate. Solvent removal afforded a liquid which was distilled, collecting the title compound at 109° C. (28 mm Hg).
Workup
- temperaturethe solution was cooled
- washThe organic layer was washed with water (4×), brine
- dry with materialdried over sodium sulfate
- customSolvent removal
- customafforded a liquid which
- distillationwas distilled
- customcollecting the title compound at 109° C. (28 mm Hg)
Sources & evidence
- ORD record
- ord-756f481218f849eb804b512e03a2efa7
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05936000
Reaction notes
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