Water → HCID 13687912, compound

HRID 569794Notes

Reaction equation

HRID 569794 reaction equation
C[Si](C)(C)Cl.[C:6]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:19](O)[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH:15]=2)[CH:10]=1)(=[O:8])C.[CH2:27](N(CC)CC)C.[OH-:34].[Na+].BrBr.[OH2:38]>ClCCl.CC(C)=O>[OH:34][CH:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:6]([O:8][CH3:27])=[O:38])[CH:18]=[CH:17]2)[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

9

Reactant 6

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24408BromineHCID 13687909HCID 13687909, compound

Product 1

HCID 13687912HCID 13687912, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

8.4 ml (66.2 mmol) of trimethylchlorosilane are added to 9.17 g (33.1 mmol) of 2-acetyl-6-(1-hydroxy-1-(3-pyridyl) methyl)naphthalene and 13.8 ml (99.3 mmol) of absolute triethylamine in 200 ml of absolute dichloromethane at 0° C., with stirring. After the mixture has stood at room temperature overnight, it is evaporated, the residue is taken up in sodium bicarbonate solution, and the solution is extracted with ethyl acetate. After drying and evaporation, the residue (12.4 g) is dissolved in 35 ml of dioxane and is added, at 0° to 10° C., to a solution of 14.2 g (0.355 mol) of sodium hydroxide in 70 ml of water, to which 5.5 ml (106.5 mmol, 17 g) of bromine have previously been added dropwise. After the mixture has stood overnight at room temperature, 10 ml of acetone are added, and the mixture is stirred for 30 minutes, extracted twice with ethyl acetate, and the aqueous phase is adjusted to pH 2 with 2 N HCl and is evaporated. The residue is then extracted by boiling with isopropanol and is evaporated. The remaining residue is taken up in 400 ml of 1 N methanolic hydrochloric acid, and the solution is allowed to stand at room temperature overnight. It is then evaporated, and the residue is taken up in sodium carbonate solution which is extracted with ethyl acetate. 4.4 g of crude product are obtained after drying and evaporation, from which 3.63 g (37%) of methyl 6-[1-hydroxy-1-(3-pyridyl) methyl]-2-naphthoate are isolated by chromatography on silica gel (ethyl acetate).

Workup

  1. customit is evaporated
  2. extractionthe solution is extracted with ethyl acetate
  3. customAfter drying
  4. customevaporation
  5. dissolutionthe residue (12.4 g) is dissolved in 35 ml of dioxane
  6. additionhave previously been added dropwise
  7. waitAfter the mixture has stood overnight at room temperature
  8. stirringthe mixture is stirred for 30 minutes
  9. extractionextracted twice with ethyl acetate
  10. customis evaporated
  11. extractionThe residue is then extracted
  12. customis evaporated
  13. waitto stand at room temperature overnight
  14. customIt is then evaporated
  15. extractionis extracted with ethyl acetate
  16. custom4.4 g of crude product are obtained
  17. customafter drying
  18. customevaporation

Sources & evidence

ORD record
ord-e823c98fdab647d9a8a2d018aceb15d8
Source dataset
uspto-grants-1988_03
Patent number
US04734406

Reaction notes

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