Malonic Acid → HCID 54430904, compound

HRID 569481

Reaction equation

HRID 569481 reaction equation
[C:1]([C:14]1[CH:18]=[CH:17][O:16][C:15]=1[CH:19]=O)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(O)(=O)[CH2:22][C:23]([OH:25])=[O:24]>CO>[C:1]([C:14]1[CH:18]=[CH:17][O:16][C:15]=1[CH:19]=[CH:22][C:23]([OH:25])=[O:24])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 201471733-(1-Tridecynyl)furan-2-carboxaldehyde

Product 1

HCID 54430904HCID 54430904, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of 3-(1-tridecynyl)furan-2-carboxaldehyde (700 mg, 2.56 mmole from Example 6) with malonic acid (535 mg, 5.12 mmole) as described in Example 2 gave 0.778 g (98%) of the title compound, mp (methanol) 71°-72° C. νmax (mull) 3140, 2600 (broad), 1680, 1630, 1465 cm-1 ; δ(DMSO) 0.80 (3H, distorted t, terminal CH3), 1.09-1.60 (18H, m, alkylene chain), 2.42 (2H, t, CH2C≡C), 6.25 (1H, d, J 15.3 Hz, C=CH--CO2H), 6.62 (1H, d, J 2 Hz, C-4H), 7.33 (1H, d, J 15.3 Hz, Ar CH=C), 7.79 (1H, d, J 2 Hz, C-5H).

Sources & evidence

ORD record
ord-c0acf803ba384fb78c7ba7322e4cabd4
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Linked notes

Loading…