Potassium Hydroxide → (E)-3-(N-ethyl-6,6-dimethyl-2-hepten-4-ynylaminomethyl) cinnamic acid

HRID 1464795Notes

Reaction equation

HRID 1464795 reaction equation
[CH2:1]([N:3]([CH2:13][C:14]1[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=1)/[CH:17]=[CH:18]/[C:19]([O:21]CC)=[O:20])[CH2:4][CH:5]=[CH:6][C:7]#[C:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2].OCC1C=C(C=CC=1)C=O.Cl.C(NC/C=C/C#CC(C)(C)C)C.OCC1OC(C=O)=CC=1.Cl.C(NC/C=C/C#CC(OC)(C)C)C.[OH-].[K+]>>[CH2:1]([N:3]([CH2:13][C:14]1[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=1)/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH2:4][CH:5]=[CH:6][C:7]#[C:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2]

Participants

7

Reactant 6

HCID 14797Potassium HydroxideHCID 2373325-(Hydroxymethyl)furfuralHCID 131314553-(Hydroxymethyl)benzaldehydeHCID 19917114(E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochlorideHCID 19917137(E)-N-ethyl-6-methoxy-6-methyl-2-hepten-4-ynylamine hydrochlorideHCID 86747792ethyl (E)-3-(N-ethyl-6,6-dimethyl-2-hepten-4-ynylaminomethyl)cinnamate

Product 1

HCID 86747791(E)-3-(N-ethyl-6,6-dimethyl-2-hepten-4-ynylaminomethyl) cinnamic acid

Procedure

When ethyl (E)-3-(N-ethyl-6,6-dimethyl-2-hepten-4-ynylaminomethyl)cinnamate, prepared by using 3-hydroxymethylbenzaldehyde and (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride instead of the starting 5-hydroxymethyl-2-furaldehyde and (E)-N-ethyl-6-methoxy-6-methyl-2-hepten-4-ynylamine hydrochloride as in Referential Example 46, is hydrolyzed with potassium hydroxide, (E)-3-(N-ethyl-6,6-dimethyl-2-hepten-4-ynylaminomethyl) cinnamic acid is obtained.

Sources & evidence

ORD record
ord-9367b6f21e454c158e26a5a1fff13a24
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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