1-Methylpiperazine → 6-Methoxy-3-pentyl-2-benzofurancarboxaldehyde

HRID 1651269Notes

Reaction equation

HRID 1651269 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].CN1CCNCC1.C([O:24][C:25]([C:27]1[O:28][C:29]2[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:30]=2[C:31]=1[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=O)C>C1(C)C=CC=CC=1>[CH3:42][O:41][C:39]1[CH:38]=[CH:37][C:30]2[C:31]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[C:27]([CH:25]=[O:24])[O:28][C:29]=2[CH:40]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 147427726-Methoxy-3-pentyl-2-benzofurancarboxylic acid ethyl esterHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 147427736-Methoxy-3-pentyl-2-benzofurancarboxaldehydeYield 94.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent4×

Procedure

As in Example 152, sodium bis(2-methoxyethoxy)aluminum hydride in toluene (3.4M; 33.6 mL) and toluene (30 mL) pretreated with N-methypiperazine (13.5 mL) in toluene (20 mL) was reacted with 6-methoxy-3-pentyl-2-benzofurancarboxylic acid ethyl ester (6 g) in toluene (90 mL) for 30 minutes at -45° C. The previously described work up yielded 4.82 g of 6-methoxy-3-pentyl-2-benzofurancarboxaldehyde as an oil.

Sources & evidence

ORD record
ord-90a2c0f0cb464bfcb8e0747d11e8a430
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

Loading…