Malonic Acid → (E)-3-[4-(1-Octynyl)-3-thienyl]prop-2-enoic acid

HRID 569495Notes

Reaction equation

HRID 569495 reaction equation
[C:1]([C:9]1[C:10]([CH:14]=O)=[CH:11][S:12][CH:13]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19]>>[C:1]([C:9]1[C:10](/[CH:14]=[CH:17]/[C:18]([OH:20])=[O:19])=[CH:11][S:12][CH:13]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 201471584-(Octynyl)-3-thiophenecarboxaldehyde

Product 1

HCID 20147160(E)-3-[4-(1-Octynyl)-3-thienyl]prop-2-enoic acidYield 41.5%

Procedure

Reaction of 4-(octynyl)-3-thiophenecarboxaldehyde (550 mg, 2.5 mmole) with malonic acid by the method described in Example 2 yielded the title compound 272 mg (41.5%) mp °C.; νmax (mull) 2600(vb), 1790, 1615, 940, 865, 835, 760; δ(CDCl3) 0.90(3H, distorted t), 1.40(8H, m), 2.37(2H, t, J=6 Hz), 6.23(1H, d, J=16 Hz), 7.22(1H, bs), 7.37(1H, bs), 7.77(1H, d, J=16 Hz), 10.3(1H, bs).

Sources & evidence

ORD record
ord-649275fa057a4c1e8bf041b032910665
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Reaction notes

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