5-acetyl-2-Furancarboxylic acid methyl ester → (E)-5-[1-methyl-2-(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)ethenyl]-2-furan carboxylic acid methyl ester

HRID 2399790Notes

Reaction equation

HRID 2399790 reaction equation
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:14]3[C:18]=2[N:17]=[C:16]2[CH2:19][CH2:20][CH2:21][CH2:22][C:15]=32)C=CC=CC=1.[CH3:43][O:44][C:45]([C:47]1[O:48][C:49]([C:52](=O)[CH3:53])=[CH:50][CH:51]=1)=[O:46]>>[CH3:43][O:44][C:45]([C:47]1[O:48][C:49](/[C:52](/[CH3:53])=[CH:9]/[C:10]2[CH:11]=[CH:12][CH:13]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:14]3[C:18]=2[N:17]=[C:16]2[CH2:19][CH2:20][CH2:21][CH2:22][C:15]=32)=[CH:50][CH:51]=1)=[O:46]

Participants

3

Reactant 2

HCID 122812255-acetyl-2-Furancarboxylic acid methyl esterHCID 19384579triphenyl-[(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)methyl]phosphonium bromide

Product 1

HCID 67784853(E)-5-[1-methyl-2-(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)ethenyl]-2-furan carboxylic acid methyl esterYield 52.5%

Procedure

Using the conditions described in Example 37, the Wittig condensation reaction of 2.8 g of the phosphonium salt from Example 26 with 0.76 g of 5-acetyl-2-furancarboxylic acid methyl ester from Example 45 produced 1.0 g (52.5%) of (E)-5-[1-methyl-2-(1,2,3,4- tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)ethenyl]-2-furan carboxylic acid methyl ester as a yellow oil after chromatographic purification.

Sources & evidence

ORD record
ord-60554bfe6d144ced8b9a5d4520338053
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

Loading…