Sodium Hydroxide → HCID 58355519, compound

HRID 1184267Notes

Reaction equation

HRID 1184267 reaction equation
O=[C:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[N:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[N+:18]=[N-:19].CO.C[O-].[Na+].[OH-].[Na+]>CO>[C:20]1([N:17]2[C:2]([CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:3]([C:4]([OH:6])=[O:5])[N:19]=[N:18]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 61162Ethyl 3-oxo-5-phenylpentanoateHCID 69319AzidobenzeneHCID 23694274Sodium methanolate methanol

Product 1

HCID 58355519HCID 58355519, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl 3-oxo-5-phenylpentanoate (1.1 g) in methanol (50 ml) was cooled to 0° C.-5° C., azidobenzene (600 mg) and 28% sodium methoxide methanol solution (965 mg) were added and the mixture was stirred at 60° C. for 3 hr. Then, 1N sodium hydroxide (10 ml) was added and the mixture was stirred at 60° C. for 1 hr. The solvent was evaporated under reduced pressure and water (20 ml) was added. 1N Hydrochloric acid was added for neutralization and the mixture was extracted with ethyl acetate (30 ml×2). The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (480 mg) as a powder.

Workup

  1. stirringthe mixture was stirred at 60° C. for 1 hr
  2. customThe solvent was evaporated under reduced pressure and water (20 ml)
  3. additionwas added
  4. addition1N Hydrochloric acid was added for neutralization
  5. extractionthe mixture was extracted with ethyl acetate (30 ml×2)
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. washa fraction eluted with ethyl acetate
  9. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-f9db5ec147534a4193dec756b50e815c
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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