Ethyl Acetate → HCID 86607166, compound

HRID 732788Notes

Reaction equation

HRID 732788 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([OH:22])=[C:17]([C:23]1[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][CH:24]=1)[CH:16]=[CH:15]2.[H-].[Na+].C(OCC)(=O)C>CN1CCCC1=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([O:22][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[C:17]([C:23]1[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][CH:24]=1)[CH:16]=[CH:15]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 685188176-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

Product 1

HCID 86607166HCID 86607166, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Add 4-fluoro-benzaldehyde (2.20 mL, 20.3 mmol) to a solution of 6-methoxy-2-(4-methylsulfanyl-phenyl)-naphthalen-1-ol (3.0 g, 10.1 mmol) and 60% sodium hydride (400 mg, 10.1 mmol) in 1-methyl-2-pyrrolidinone (30 mL). Heat the reaction to 170° C. for 70 minutes, then cool to ambient temperature. Dilute the reaction with ethyl acetate (200 mL) and wash twice with 5% aqueous lithium chloride (500 mL), brine, 1N aqueous hydrochloric acid, dry with solid magnesium sulfate and chromatograph on silica gel with dichloromethane/hexane mixtures to give 1.29 g of 4-[6-methoxy-2-(4-methylsulfanyl-phenyl)-naphthalen-1-yloxy]-benzaldehyde (32%).

Workup

  1. temperatureHeat
  2. customthe reaction to 170° C. for 70 minutes
  3. additionDilute
  4. washwash twice with 5% aqueous lithium chloride (500 mL), brine, 1N aqueous hydrochloric acid
  5. dry with materialdry with solid magnesium sulfate and chromatograph on silica gel with dichloromethane/hexane

Sources & evidence

ORD record
ord-28700a8867504340a77017dc8587ac4b
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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