Water → 2-(4-Methoxyphenyl)-3-(3-hydroxyphenyl)-6-methoxybenzo[b]thiophene

HRID 1954183Notes

Reaction equation

HRID 1954183 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26]CC3C=CC=CC=3)[CH:21]=2)=[CH:5][CH:4]=1.O.C([O-])=O.[NH4+]>CCO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 232963102-(4-Methoxyphenyl)-3-(3-benzyloxyphenyl)-6-methoxybenzo[b]thiophene

Product 1

HCID 154853032-(4-Methoxyphenyl)-3-(3-hydroxyphenyl)-6-methoxybenzo[b]thiophene

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry was prepared consisting of 2-(4-methoxyphenyl)-3-(3-benzyloxyphenyl)-6-methoxybenzo[b]thiophene in 1 L of EtOH, 250 mL of EtOAc, and 40 mL of water. Palladium(0) black 4.04 g (38 mmol) and ammonium formate 12.6 g (200 mmol) was added. The reaction mixture was heated to reflux for one hour, then filtered hot through celite and evaporated to dryness. The solid was partioned between EtOAc and a saturated solution of Na2HCO3. The organic layer was washed with brine, dried with Na2SO4, and evaporated to dryness. This yielded 12.8 g of the title compound as a white solid.

Workup

  1. customA slurry was prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for one hour
  4. filtrationfiltered hot through celite
  5. customevaporated to dryness
  6. washThe organic layer was washed with brine
  7. dry with materialdried with Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-f91aa5ec0d9a486794c049fe80551eff
Source dataset
uspto-grants-2000_09
Patent number
US06121293

Reaction notes

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