Methanol → HCID 53697716, compound

HRID 1419254Notes

Reaction equation

HRID 1419254 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:15])=O.[Br-].[CH2:17]([O:19][C:20]([CH2:22][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:21])[CH3:18].C(=O)([O-])[O-].[K+].[K+].CO>CN(C=O)C>[C:13]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[C:3]([CH:1]=[CH:22][C:20]([O:19][CH2:17][CH3:18])=[O:21])=[C:4]([OH:15])[CH:5]=[CH:6]2)#[N:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 73731(Ethoxycarbonylmethyl)triphenylphosphonium bromideHCID 532566235-Formyl-6-hydroxy-2-naphthonitrile

Product 1

HCID 53697716HCID 53697716, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution prepared by dissolving 19.3 g of 1-formyl-6-cyano-2-naphthol and 42.1 g of ethoxycarbonylmethyltriphenylphosphonium bromide in 140 ml of DMF was added dropwise to a solution comprising 13.6 g of anhydrous potassium carbonate and 250 ml of anhydrous methanol, followed by stirring for 3 hours under cooling with ice in a nitrogen stream and 24 hours at room temperature. The precipitate was filtered, and 2.7 liters of water was added to the filtrate, followed by stirring for 2 hours. Then, the precipitate was collected by filtration and washed with 90 ml of methanol to obtain 12.6 g of the desired product.

Workup

  1. customA solution prepared
  2. additionwas added dropwise to a solution
  3. filtrationThe precipitate was filtered
  4. addition2.7 liters of water was added to the filtrate
  5. stirringby stirring for 2 hours
  6. filtrationThen, the precipitate was collected by filtration
  7. washwashed with 90 ml of methanol

Sources & evidence

ORD record
ord-008a80a6c0164c4da077e2ad7ff06b79
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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