HCID 10667130, compound → HCID 10785526, compound

HRID 1386988Notes

Reaction equation

HRID 1386988 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:18]3[CH:33]=[CH:32][CH:31]=[CH:30][C:19]=3[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=O)=[CH:11][CH:10]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]2[S:20][C:19]3[CH:30]=[CH:31][CH:32]=[CH:33][C:18]=3[C:17]=2[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[CH2:1])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 10667130HCID 10667130, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10785526HCID 10785526, compoundYield 170.6%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.20 g (3.36 mmol) of methyltriphenylphosphonium bromide in 50 mL of THF was treated with 0.45 g (4.01 mmol) of potassium tert-butoxide and the mixture stirred at room temperature for 0.5 h. To this was added dropwise 0.80 g (2.14 mmol) of 2-(4-methoxyphenyl)benzo[b]thiophen-3-yl 4-methoxyphenyl ketone (Example 3, Part B) in 10 mL of THF and the reaction was stirred at room temperature for 18 h and then heated at gentle reflux for 48 h. The reaction was quenched by 100 mL of brine. The two layers were separated and the organic layer was dried over Na2SO4. Concentration in vacuo gave 1.36 g of an oil which was purified by radial chromatography (SiO2; 10% EtOAc in hexanes) to afford 0.610 g (1.64 mmol; 77%) of the desired product as an oil.

Workup

  1. stirringthe reaction was stirred at room temperature for 18 h
  2. temperatureheated
  3. temperatureat gentle reflux for 48 h
  4. customThe reaction was quenched by 100 mL of brine
  5. customThe two layers were separated
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-ec65efdd2dfb419eb241613cdc72291b
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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