Sodium hydride → HCID 20205045, compound

HRID 978078Notes

Reaction equation

HRID 978078 reaction equation
[CH2:1]([S:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:10]=1[C:11]([O:13]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O>[OH:13][C:11]1[C:10]2[C:15]([O:19][CH3:20])=[CH:16][CH:17]=[CH:18][C:9]=2[S:8][C:1]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 20205048HCID 20205048, compound

Product 1

HCID 20205045HCID 20205045, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of methyl 2-benzylthio-6-methoxybenzoate (0.50 g, 1.7 mmol) in N,N-dimethylformamide (2 ml) was added dropwise with stirring under a nitrogen atmosphere to a suspension of sodium hydride (50% dispersion in mineral oil) (90 mg, 1.9 mmol) in N,N-dimethylformamide (5 ml) at room temperature. The mixture was stirred at 80° C. for 2 hours and then at 100° C. for 10 hours. The cooled mixture was then poured into ice containing 2N hydrochloric acid and extracted with diethyl ether. The combined organic layers were washed with water (3×), saturated aqueous sodium chloride solution, dried (sodium sulfate), and evaporated. The residue was vacuum filtered through a pad of silica gel (Merck No. 7734), eluting with 2:1 hexane-ether. Fractions containing pure product were evaporated, and the resulting syrup triturated with methanol to afford 3-hydroxy-4-methoxy-2-phenylbenzo[b]thiophene as a white solid; yield 0.12 g (27%); m/z 256 (M30. ).

Workup

  1. waitat 100° C. for 10 hours
  2. extractionextracted with diethyl ether
  3. washThe combined organic layers were washed with water (3×), saturated aqueous sodium chloride solution
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. filtrationfiltered through a pad of silica gel (Merck No
  7. wash7734), eluting with 2:1 hexane-ether
  8. additionFractions containing pure product
  9. customwere evaporated
  10. customthe resulting syrup triturated with methanol

Sources & evidence

ORD record
ord-1af1a6d1d4d944668a30cdecb2e5cd44
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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