Tributylphosphine → HCID 19752431, compound

HRID 2244027Notes

Reaction equation

HRID 2244027 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][OH:12])[N:6]=1)=[O:4].[OH:13][C:14]1[C:19]([CH2:20][CH2:21][CH3:22])=[C:18](O)[CH:17]=[CH:16][C:15]=1[C:24](=[O:26])[CH3:25].C(P(CCCC)CCCC)CCC.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>C1COCC1.C(OCC)(=O)C.C(OCC)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][C:18]2[CH:17]=[CH:16][C:15]([C:24](=[O:26])[CH3:25])=[C:14]([OH:13])[C:19]=2[CH2:20][CH2:21][CH3:22])[N:6]=1)=[O:4]

Participants

8

Reactant 4

HCID 13831TributylphosphineHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 11513809Methyl 6-(hydroxymethyl)picolinateHCID 14357405Diethyldiazodicarboxylate

Product 1

HCID 19752431HCID 19752431, compoundYield 83.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 6-hydroxymethyl-pyridine-2-carboxylic acid methyl ester (2.20 g, 13.2 mmol), 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (2.56 g, 13.2 mmol), and tri-n-butylphosphine (3.94 mL, 15.8 mmol) in THF (45 mL). Add diethyl diazodicarboxylate (3.98 g, 15.8 mmol). After 12 hours at ambient temperature, add diethyl ether (white precipitate forms) and filter, collect liquid and remove solvents under reduced pressure. Purify residue by flash chromatography eluting with 3:7 hexane:ethyl acetate to obtain the title compound as a white solid (3.769 g, 10.98 mmol): mass spectrum (m/e): 344 (M+1).

Workup

  1. filtrationfilter
  2. customcollect liquid
  3. customremove solvents under reduced pressure
  4. washPurify residue by flash chromatography eluting with 3:7 hexane

Sources & evidence

ORD record
ord-074d67d40826462593ba9691cdcd6130
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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