HCID 15078761, compound → HCID 15078748, compound

HRID 359155Notes

Reaction equation

HRID 359155 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][S:5]/[C:6](/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:7]\[C:8]([O:10]C)=O.CC(C)([O-])C.[K+]>C1COCC1>[OH:10][C:8]1[CH:7]=[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:5][C:4]=1[C:3]1[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 15078761HCID 15078761, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15078748HCID 15078748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of methyl Z-3-(2'-methylbenzylthio)-3-phenyl-2-propenoate (900 mg, 3.02 mmol) in THF (8 mL) was added dropwise through a double-ended needle to a solution of potassium tert-butoxide (1.02 g, 9.09 mmol) in THF (12 mL). An additional 2 mL of THF was used to rinse the ester into the reaction. The reaction was stirred 30 minutes at 25° C., then cooled in an ice bath and quenched by the addition of 7.0 mL of 2.0 N aqueous hydrochloric acid. The reaction was poured into 50 mL of saturated aqueous sodium chloride solution and extracted with 2×50 mL of ethyl acetate. The ethyl acetate layers were washed in succession with 50 mL of saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and evaporated. Flash column chromatography on 45 g of silica gel, eluting with 500 mL of 4% ethyl acetate in hexane followed by 500 mL of 6% ethyl acetate in hexane, gave 3-hydroxy-2-(2'-methyl phenyl) 5-phenylthiophene as an oil weighing 421 mg. The product could be distilled bulb-to-bulb, bp (0.4 mm) 140°-150° C.

Workup

  1. washto rinse the ester
  2. custominto the reaction
  3. temperaturecooled in an ice bath
  4. customquenched by the addition of 7.0 mL of 2.0 N aqueous hydrochloric acid
  5. additionThe reaction was poured into 50 mL of saturated aqueous sodium chloride solution
  6. extractionextracted with 2×50 mL of ethyl acetate
  7. washThe ethyl acetate layers were washed in succession with 50 mL of saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. washFlash column chromatography on 45 g of silica gel, eluting with 500 mL of 4% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a4e79628ab844615a17628f0f66878c3
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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