Pivaloyl chloride → HCID 72326552, compound
Reaction equation
[C:1]([C:3](=[C:9]([OH:15])[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].O(C)[Na].[Na].[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>C(O)C.C(#N)C>[C:1]([C:3](=[C:9]([O:15][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]Participants
Conditions
- Temperature
- 20 °C
Procedure
36 g (0.17 mol) of ethyl 2-cyano-3-hydroxy-4-ethyl-2-hexenoate were dissolved in ethanol, and 31 g (0.17 mol) of 30% strength NaOCH3 solution were added. The mixture was then concentrated to dryness, and the sodium enolate was released by adding toluene and reconcentration of alcohol residues. 39.7 g (0.17 mol) of the resulting sodium salt were initially charged in acetonitrile and, at 0° C. with warming to 20° C., mixed dropwise with 27.4 g (0.23 mol) of pivaloyl chloride. After 16 g of stirring at 25° C., the reaction mixture was concentrated and the residue was taken up in ethyl acetate and washed with 2% strength NaOH. The organic phase was dried and concentrated. Customary purification gave 41.5 g (83% of theory) of the title compound (b.p. 102° C./1 mbar).
Workup
- concentrationThe mixture was then concentrated to dryness
- additionby adding toluene and reconcentration of alcohol residues
- concentrationthe reaction mixture was concentrated
- washwashed with 2% strength NaOH
- customThe organic phase was dried
- concentrationconcentrated
- customCustomary purification
Sources & evidence
- ORD record
- ord-b6085746bd62423b88323e81e79048af
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842832B2
Reaction notes
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