Sodium hydride → HCID 53775193, compound

HRID 322973Notes

Reaction equation

HRID 322973 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[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:35])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[Cl:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[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]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10657149HCID 10657149, compoundHCID 54244821HCID 54244821, compound

Product 1

HCID 53775193HCID 53775193, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4-(3-thienylmethoxy)benzonitrile (0.5 g) is added portionwise to a stirred suspension of sodium hydride (90 mg, 60% dispersion in mineral oil) in dry DMF (100 mL). After stirring at ambient temperature for 30 minutes, ethyl (RS)-4-chloro-4-(2-chloro-6-fluorophenyl)butanoate (0.62 g) is added in one portion and the reaction stirred for 48 hours at 90° C. The reaction mixture 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 residue 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-chloro-6-fluorophenyl)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)butanoate (360 mg) as an orange oil.

Workup

  1. stirringthe reaction stirred for 48 hours at 90° C
  2. concentrationThe reaction mixture 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 residue 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-828e31278bb9460c8fdf3956eb03445d
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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