Sodium hydride → HCID 54574257, compound

HRID 322992Notes

Reaction equation

HRID 322992 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].Cl[CH:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]#[N:35])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C)C=O>[C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH:20]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10657149HCID 10657149, compoundHCID 53919123HCID 53919123, compound

Product 1

HCID 54574257HCID 54574257, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4-(3-thienylmethoxy)benzonitrile (2.5 g) is added portionwise to a stirred suspension of sodium hydride (0.44 g, 60% dispersion in mineral oil) in dry dimethyl formamide (30 mL). After stirring at ambient temperature for 30 minutes, ethyl (RS)-4-chloro-4-(2-cyanophenyl)butanoate (2.87 g) is added in one portion and the reaction stirred for 16 hours at 100° C. The reaction is concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase is dried over magnesium sulphate, filtered and concentrated in vacuo. The residual oil is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2 v/v). Fractions homogeneous in the required product are combined and evaporated to give ethyl (RS)-4-(2-cyanophenyl)-4-[2-cyano-5-(3-thienylmethoxy)phenoxy]butanoate (250 mg) as an orange oil.

Workup

  1. stirringthe reaction stirred for 16 hours at 100° C
  2. concentrationThe reaction is concentrated in vacuo
  3. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual oil is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2 v/v)
  8. customevaporated

Sources & evidence

ORD record
ord-bff197cd75244f6bba849616f024b7f3
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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