Malonic Acid → HCID 20147154, compound

HRID 569490Notes

Reaction equation

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

Participants

Reactant 2

HCID 867Malonic Acid

HCID 20147157HCID 20147157, compound

Product 1

HCID 20147154HCID 20147154, compoundYield 93.5%

Procedure

Reaction of 5-(1-octynyl)-2-thiophene carboxaldehyde (880 mg, 4 mmole) with malonic acid as described in Example 2 yielded 0.98 g (93.5%) of the title compound after recrystallization from hexane mp 79° C.; νmax (mull) 2600 (broad), 1690, 1670, 1610, 940, 845, 800; δ(CDCl3) 0.90(3H, t, J=6 Hz), 1.50(8H, m), 2.40(2H, t, J=6 Hz), 6.15(1H, d, J=15 Hz), 7.05(1H, d, J=4.5 Hz), 7.13(1H, d, J=4.5 Hz), 7.85(1H, d, J=15 Hz), 11.3(1H, bs). M+ 262.1022 C15H15O2S requires 262.1027. Found; C, 68.96; H, 7.14; C15H15O2S requires; C, 68.68; H, 6.92.

Sources & evidence

ORD record: ord-77741e0364904ed1aada57fd6cef8e9a
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04732901

Reaction notes

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