Acetic Acid → HCID 67785432, compound

HRID 2399807Notes

Reaction equation

HRID 2399807 reaction equation
[CH2:1]([CH:9]1[C:14]2=[C:15]3[CH2:21][CH2:20][CH2:19][CH2:18][C:16]3=[N:17][C:13]2=[C:12]([C:22]([C:24]2[O:28]C(C=O)=[CH:26][CH:25]=2)=[O:23])[CH:11]=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C-:31]#N.[Na+].[C:34]([OH:37])(=[O:36])[CH3:35]>CO.[O-2].[O-2].[Mn+4]>[CH3:31][O:36][C:34]([C:35]1[O:28][C:24]([C:22]([C:12]2[CH:11]=[CH:10][CH:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:14]3[C:13]=2[N:17]=[C:16]2[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=32)=[O:23])=[CH:25][CH:26]=1)=[O:37]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 19384475HCID 19384475, compound

Product 1

HCID 67785432HCID 67785432, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 3.7 g of the aldehyde derivative from Example 155, 2.0 g of sodium cyanide and 10 g of activated manganese dioxide in 200 mL of methanol was added 1.0 g of acetic acid at room temperature. The reaction mixture was stirred for 2 hours at room temperature, filtered on celite and extracted with ethyl acetate. The crude material (3.5 g) was purified on a short pad of silica gel giving 2.9 g (73%) of 5-[(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)carbonyl]-2-furancarboxylic acid methyl ester as a yellow oil.

Workup

  1. filtrationfiltered on celite
  2. extractionextracted with ethyl acetate
  3. customThe crude material (3.5 g) was purified on a short pad of silica gel giving 2.9 g (73%) of 5-[(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)carbonyl]-2-furancarboxylic acid methyl ester as a yellow oil

Sources & evidence

ORD record
ord-dfe94bb5e6794b14b5d11c61033a9212
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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