Hexane → HCID 13502056, compound
Reaction equation
[CH3:1][S:2]([CH:5]=[CH2:6])(=[O:4])=[O:3].C(N(CC)CC)C.[C:14]([OH:17])(=[S:16])[CH3:15].CCCCCC>CO.C(OCC)(=O)C>[C:14]([S:16][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:17])[CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 53.2 g (0.5 mole) methylvinylsulfone and 1 ml triethylamine in 50 ml methanol, 38.06 g [35.75 ml (0.5 mole)] thioacetic acid was added dropwise over 15 minutes. During the addition, the temperature was maintained between 30°-40° C. with an ice bath. The mixture was stirred overnight at room temperature; then the solvent was removed using a rotovap to give a yellow-red oil which solidified upon cooling. The residue was dissolved in 150 ml of hot ethyl acetate; then 100 ml hexane was added. With cooling of the solution in an ice bath, fine white needle crystals formed. The crystals were recovered by filtration, were washed with cold 1:1 ethyl acetate:hexane and air-dried to give 35.28 g of the above-identified product as a crystalline solid, melting point 57°-59° C. A second crop of 29.13 g crystals melting point 57°-60° C. was obtained to give a total of 64.41 g of the above-identified product.
Workup
- additionDuring the addition
- temperaturethe temperature was maintained between 30°-40° C. with an ice bath
- customthen the solvent was removed
- customto give a yellow-red oil which
- temperatureupon cooling
- temperatureWith cooling of the solution in an ice bath
- customfine white needle crystals formed
- filtrationThe crystals were recovered by filtration
- washwere washed with cold 1:1 ethyl acetate
- dry with materialhexane and air-dried
Sources & evidence
- ORD record
- ord-5e252b5f8a564454924299e558dd54f0
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04652556
Reaction notes
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