Sodium hydride → HCID 22010371, compound

HRID 322907Notes

Reaction equation

HRID 322907 reaction equation
[H-].[Na+].[OH:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[CH2:5][CH2:6][CH2:7][C:8]([O-:10])=[O:9].[Na+].F[C:20]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)[CH:25]=[CH:24][C:21]=1[C:22]#[N:23]>O1CCCC1>[C:22]([C:21]1[CH:24]=[CH:25][C:26]([O:28][CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[CH:27][C:20]=1[O:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])#[N:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 107283302-Fluoro-4-(3-thienylmethoxy)benzonitrileHCID 86756591HCID 86756591, compound

Product 1

HCID 22010371HCID 22010371, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
57.5 °C

Procedure

To a stirred suspension of sodium hydride (0.69 g, 60% dispersion in mineral oil) in dry tetrahydrofuran (50 mL) is added a solution of sodium (RS)-5-hydroxy-5-(2-methylphenyl)pentanoate (1.23 g) in dry tetrahydrofuran (100 mL). The mixture is stirred at room temperature for 1.5 hours when 2-fluoro-4-(3-thienylmethoxy)benzonitrile (1.57 g) is added in one portion. The reaction mixture is heated at 55-60° C. for 18 hours and evaporated. The residue is dissolved in water (100 mL), the solution acidified to pH 1 with 1 N hydrochloric acid and the mixture extracted three times with ethyl acetate (100 mL). The combined extracts are washed with brine (100 mL), dried over magnesium sulphate and evaporated to give (RS)-5-[2-cyano-5-(3-thienylmethoxy)phenoxy]-5-(2-methylphenyl)pentanoic acid as a white waxy solid (0.4 g), mp.p.106-108° C. [Elemental analysis:- C,67.15; H,5.84; N,2.75; S,6.99%. Calculated for C24H23NO4S.0.5EtOAc:- C,66.66; H,4.66; N,6.48%].

Workup

  1. additionis added in one portion
  2. customevaporated
  3. dissolutionThe residue is dissolved in water (100 mL)
  4. extractionthe mixture extracted three times with ethyl acetate (100 mL)
  5. washThe combined extracts are washed with brine (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-e5a75c5bb54847a3a3d45b1855dacd4b
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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