HCID 22461690, compound → Ethyl 4-(3-cyano-4-hydroxyphenyl)butanoate

HRID 1937783Notes

Reaction equation

HRID 1937783 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[OH:8].[C:17]([Cu])#[N:18]>CN1CCCC1=O.CCOC(C)=O>[C:17]([C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[OH:8])#[N:18]

Participants

5

Reactant 2

HCID 22461690HCID 22461690, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22461719Ethyl 4-(3-cyano-4-hydroxyphenyl)butanoate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of ethyl 4-(3-bromo-4-hydroxyphenyl)butanoate (19.8 g, 69 mmol) in 172 mL of N-methyl-2-pyrrolidinone was added CuCN (6.49 g, 72.4 mmol). The solution was heated to reflux for 4 hours then cooled to room temperature. The reaction was diluted with EtOAc and washed twice with 5% HCl and once with brine, then dried over sodium sulfate and concentrated. Purified on silica gel using 60:40 hexanes:EtOAc as the elutant. The yield of ethyl 4-(3-cyano-4-hydroxyphenyl)butanoate was 9.84 g (61%): 1H-NMR (CDCl3) 7.67 (1H, s), 7.24-7.29 (2H), 7.94 (1H, d), 4.14 (2H, q), 2.59 (2H, dd), 2.34 (2H, dd), 1.91 (2H, m), 1.28 (3H, t).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 4 hours
  3. washwashed twice with 5% HCl and once with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurified on silica gel using 60:40 hexanes

Sources & evidence

ORD record
ord-33a3f30bcd04423188eb2d3058795daf
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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