HCID 21514870, compound → 1-Heptene
Reaction equation
[C:1]1([CH:7]([CH:12](OS(C)(=O)=O)[CH2:13][CH2:14]CC)C=S(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Na].[Hg]>[CH3:3][CH:2]=[CH:1][CH2:7][CH2:12][CH2:13][CH3:14].[CH2:7]=[CH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
5
Reactant 1
Product 2
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -30 °C
Procedure
Following the procedure of Example 1, 0.850 g of phenylethyl sulphone and 0.430 g of valeric aldehyde were condensed with n-butyl lithium. Methyl sulphonic acid chloride was then added and, after standing overnight at -30°C, the reaction mixture was treated in the usual way, giving 1.72 g of a yellow oil which was 2-phenyl sulphonyl-3-mesyloxy heptane. 282 mg of this product in solution in methanol were then reduced by the addition of 1.5 g of 6 % sodium amalgam, followed by stirring overnight at -30°C. The upper decanted layer was analysed by vapour-phase chromatography. 2-Heptene was obtained in a yield of 80 % without any traces either of 1-heptene or of 3-heptene.
Sources & evidence
- ORD record
- ord-ba6935e32fe74339beebc43313cac8bf
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03979471
Reaction notes
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