HCID 15078760, compound → HCID 15078747, compound

HRID 359154Notes

Reaction equation

HRID 359154 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[C:8](/[S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:9]/[C:10]([O:12]C)=O.CC(C)([O-])C.[K+]>C1COCC1>[OH:12][C:10]1[CH:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[S:14][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 15078760HCID 15078760, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15078747HCID 15078747, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of methyl Z-3-(2'methylphenyl)-3-benzylthio-2-propenoate (575 mg, 1.93 mmol) in 6.0 mL of THF was added through a double ended needle to a solution of potassium tert-butoxide (650 mg, 5.79 mmol) in 8.0 mL of THF at ambient temperature. An additional 2×1 mL of THF was used to rinse the ester into the reaction. The bright orange-green reaction as stirred 20 minutes at 25° C., then cooled in an ice bath and quenched by the addition of 3.5 mL of 2.0 N aqueous hydrochloric acid. The reaction was poured into 25 mL of saturated aqueous sodium chloride and extracted with 2×25 mL of ethyl acetate. The ethyl acetate layers were washed in succession with 25 mL of saturated aqueous sodium chloride, combined, dried over sodium sulfate, decanted, and evaporated. Flash column chromatography on 15 g of silica gel eluted with 500 mL of 3% ethyl acetate in hexane followed by 200 mL of 6% ethyl acetate in hexane gave 3-hydroxy-5-(2'-methylphenyl)-2-phenylthiophene as 385 mg of pale yellow viscous oil (75% yield). The product could be distilled bulb to bulb, bp (0.4 mm) 140° -150° C.

Workup

  1. customat ambient temperature
  2. washto rinse the ester
  3. custominto the reaction
  4. customThe bright orange-green reaction
  5. temperaturecooled in an ice bath
  6. customquenched by the addition of 3.5 mL of 2.0 N aqueous hydrochloric acid
  7. additionThe reaction was poured into 25 mL of saturated aqueous sodium chloride
  8. extractionextracted with 2×25 mL of ethyl acetate
  9. washThe ethyl acetate layers were washed in succession with 25 mL of saturated aqueous sodium chloride
  10. dry with materialdried over sodium sulfate
  11. customdecanted
  12. customevaporated
  13. washFlash column chromatography on 15 g of silica gel eluted with 500 mL of 3% ethyl acetate in hexane

Sources & evidence

ORD record
ord-86c806a06fa64b74ac8665646e71cd6d
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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