Hydrochloric Acid → 2-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

HRID 354085Notes

Reaction equation

HRID 354085 reaction equation
C(S)C.C([Li])CCC.[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=3)=[O:20])=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[S:16][C:15]=2[CH:37]=1.Cl>O1CCCC1.CN(C)C=O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19]([C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)=[O:20])=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[S:16][C:15]=2[CH:37]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 9953060LY88074 Trimethyl etherHCID 178418339Butyllithium

Product 1

HCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethanethiol (538 mL, 7.27 mmol) in 1.88 mL of tetrahydrofuran, cooled to −30° C. was added n-butyllithium (2.57 mL, 2.5 M, 6.42 mmol) and the reaction was warmed to room temperature. Dimethylformamide (1 mL) was added then the product from Step 1 (1.73 g, 4.3 mmol) in 2.7 mL of dimethylformamide. The reaction was heated at 58° C. for two hours then at 80° C. for 1 hour. The cooled reaction was poured into 33 mL oh 1N hydrochloric acid and extracted with ethyl acetate. The combined organic layers was washed with brine and dried over anhydrous magnesium sulfate. After filtration, concentration and silica gel column chromatography using 15% ethyl acetate -hexanes as eluant the title compound (1.17 g) was obtained.

Workup

  1. temperatureThe reaction was heated at 58° C. for two hours
  2. customThe cooled reaction
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration, concentration and silica gel column chromatography
  7. customwas obtained

Sources & evidence

ORD record
ord-833a6e54d2d04733b394359c809d7828
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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