HCID 15078759, compound → HCID 15078743, compound

HRID 359152Notes

Reaction equation

HRID 359152 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][S:14]/[C:15](/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16]\[C:17]([O:19]C)=O)=[CH:11][CH:10]=1>C1COCC1>[OH:19][C:17]1[CH:16]=[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:14][C:13]=1[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 15078759HCID 15078759, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15078743HCID 15078743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

Potassium tert-butoxide (2.11 g, 18.8 mmol) was dissolved in 30 mL of THF at 25° C. A solution of crude methyl Z-3-(4'-methoxybenzylthio)-3-phenyl-2-propenoate (2.00 g, 6.36 mmol) in 10 mL of THF was added over 5-10 minutes. An additional 2×2 mL of THF was used to rinse the starting material into the reaction. After stirring an additional 1 hour at 25° C., the reaction was quenched with 1.5 mL of glacial acetic acid and poured into 100 mL of ethyl acetate. After washing successively with 50 mL of saturated aqueous sodium chloride, 15 mL of 2N ag. hydrochloric acid, and 50 mL of saturated ag. sodium chloride, the solution was dried over sodium sulfate, decanted, and evaporated. The residue was dissolved in dichloromethane and evaporated onto 10 g of silica gel. Flash column chromatography on 60 g of silica gel eluted with 1 L of 10% ethyl acete in hexane followed by 500 mL of 12% ethyl acetate in hexane gave 3-hydroxy-2-(4'-methoxyphenyl)-5-phenylthiophene as 0.35 g of off-white crystals.

Workup

  1. washto rinse the starting material
  2. custominto the reaction
  3. customthe reaction was quenched with 1.5 mL of glacial acetic acid
  4. additionpoured into 100 mL of ethyl acetate
  5. washAfter washing successively with 50 mL of saturated aqueous sodium chloride, 15 mL of 2N ag
  6. dry with materialsodium chloride, the solution was dried over sodium sulfate
  7. customdecanted
  8. customevaporated
  9. dissolutionThe residue was dissolved in dichloromethane
  10. customevaporated onto 10 g of silica gel
  11. washFlash column chromatography on 60 g of silica gel eluted with 1 L of 10% ethyl acete in hexane

Sources & evidence

ORD record
ord-8f5536b75cb5485faf22db8517a52f2d
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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