Malonic Acid → HCID 20147175, compound

HRID 569483Notes

Reaction equation

[C:1]([C:9]1[O: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[O: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 20147162HCID 20147162, compound

Product 1

HCID 20147175HCID 20147175, compoundYield 88.2%

Procedure

Reaction of 5-(1-octynyl)furan-2-carboxaldehyde (0.72 g, 3.5 mmole from example 8) with malonic acid (0.73 g, 7 mmole) as described in Example 2 gave 0.76 g (88%) of the title compound, mp(Hexane) 100°-100.5° C. νmax (mull) 2650 (broad), 1695, 1630, 1565, 1510, 1410, 1300, 1235, 1210 cm-1 ; δ(CDCl3) 0.90(3H, t, 6.8 Hz), 1.32(4H, m), 1.44(2H, m), 1.62(2H, m), 2.47(2H, t, J=6.5 Hz), 6.38(1H, d, J=15 Hz), 6.54(1H, d, J=3 Hz), 6.64(1H, d, J=3 Hz), 7.48(1H, d, J=15 Hz), 10.53 (1H, broad).

Sources & evidence

ORD record: ord-b2efa2be7e7445569ea562c969600be6
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04732901

Reaction notes

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