Triethylamine → n-Propyl 2-cyano-3-hydroxy-4-[(methylsulfanyl)methyl]-2-hexenoate

HRID 1176812Notes

Reaction equation

[CH3:1][S:2][CH2:3][CH:4]([CH2:8][CH3:9])[C:5](Cl)=[O:6].[C:10]([CH2:12][C:13]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])#[N:11].C(N(CC)CC)C>C(Cl)Cl>[C:10]([C:12](=[C:5]([OH:6])[CH:4]([CH2:3][S:2][CH3:1])[CH2:8][CH3:9])[C:13]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])#[N:11]

Participants

Conditions

Temperature: 0 °C

Procedure

At 25° C., 16.7 g (0.1 mol) of 2-[(methylsulfanyl)methyl]butyryl chloride were added to a solution of 12.7 g (0.1 mol) of n-propyl cyanoacetate in CH2Cl2, and the mixture was cooled to 0° C. At 0° C., 20.2 g (0.2 mol) of triethylamine were then added dropwise. After 16 h of stirring at 25° C., the reaction mixture was hydrolyzed and the organic phase was separated off, dried and concentrated. Customary purification gave 15 g (58% of theory) of the title compound as a yellow liquid (b.p. 118 to 120° C./2 mbar).

Workup

customthe organic phase was separated off
customdried
concentrationconcentrated
customCustomary purification

Sources & evidence

ORD record: ord-680d2074c566480ea36142342de8dddc
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842832B2

Reaction notes

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