Potassium Hydroxide → HCID 15044975, compound

HRID 728065Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([C:43]#[N:44])([CH2:21][CH2:22][C:23]([C:41]#[N:42])([C:29]2[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=2)C(OCC)=O)C(OCC)=O)[CH:6]=[C:7]([S:13][CH3:14])[C:8]=1[O:9][CH2:10][CH2:11][CH3:12].[OH-].[K+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]([CH2:21][CH2:22][CH:23]([C:29]2[CH:30]=[C:31]([O:39][CH3:40])[C:32]([O:37][CH3:38])=[C:33]([O:35][CH3:36])[CH:34]=2)[C:41]#[N:42])[C:43]#[N:44])[CH:6]=[C:7]([S:13][CH3:14])[C:8]=1[O:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of diethyl 2-(3-methoxy-5-(methylthio)-4-propoxyphenyl)-2,5-dicyano-5-(3,4,5-trimethoxyphenyl)-1,6-hexanedioate (12.0 g, 0.019 mol) in ethanol (250 ml) was added potassium hydroxide (4.4 g, 0.079 mol). The reaction was heated to 95° C. for 20 minutes, then filtered, and the filtrate concentrated. Methanol (300 ml) was added to the residue, and the solution was stirred at room temperature overnight. The reaction was filtered and the precipitate dried to yield 2-(3-methoxy-5-(methylthio)-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,6-hexanedinitrile in a 66% yield. (m.p. 131°-132.5° C.).

Workup

filtrationfiltered
concentrationthe filtrate concentrated
additionMethanol (300 ml) was added to the residue
filtrationThe reaction was filtered
customthe precipitate dried

Sources & evidence

ORD record: ord-8ce5ad80418c4ae29aff5dce5e61a892
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047420

Reaction notes

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