Potassium Hydroxide → HCID 21684200, compound

HRID 654626Notes

Reaction equation

COC1C=C([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)C=C(SC)C=1OCCC.[OH-].[K+]>C(O)C>[CH3:40][O:39][C:31]1[CH:30]=[C:29]([CH:23]([C:41]#[N:42])[CH2:22][CH2:21][CH2:15][C:43]#[N:44])[CH:34]=[C:33]([O:35][CH3:36])[C:32]=1[O:37][CH3:38]

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.). NMR (CDCl3): δ 1.04 (t, 3H, term CH3), 1.80 (m, 2H, OCH2CH2CH3), 2.18 (m, 2H, CH2 from ##STR30## 2.44 (m+s, SCH3 --CH2 from ##STR31## 3.90 (m, 14H, --OCH3 +OCH2CH2CH3), 6.64+6.72 (s, 2H, ArH), 6.71, 6.77, 6.81, 6.83 (d,d, 2H, ArH).

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-5c905bbaf6a54d20a0c31fa932f96650
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05132463

Reaction notes

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