Ethanol → HCID 18793057, compound

HRID 850648Notes

Reaction equation

HRID 850648 reaction equation
Br[C:2]1[C:6]([CH2:7][CH2:8][CH2:9][CH3:10])=[CH:5][S:4][C:3]=1[CH:11]=[O:12].C([O-])([O-])=O.[Na+].[Na+].CCO.[CH3:22][O:23][CH2:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1B(O)O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:7]([C:6]1[C:2]([C:27]2[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:26]=2[O:25][CH2:24][O:23][CH3:22])=[C:3]([CH:11]=[O:12])[S:4][CH:5]=1)[CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 15402632Boronic acid, [4-methoxy-2-(methoxymethoxy)phenyl]-HCID 187930493-Bromo-4-n-butylthiophene-2-carboxaldehyde

Product 1

HCID 18793057HCID 18793057, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3-Bromo-4-n-butylthiophene-2-carboxaldehyde of Example 1(b) 1.87 g, 7.57 mmol) in toluene (35 mL) was added (PPh3)4Pd (0.30 g, 0.20 mmol), Na2CO3 (2 M, 9 mL), EtOH (25 mL) and (2-methoxymethoxy-4-methoxyphenyl)boronic acid (1.76 g, 8.30 mmol), respectively. The resulting mixture was stirred at reflux for 3 h. After quenching with water and extraction with EtOAc, the organic extract was washed with H2O, brine and dried (MgSO4). The solvent was removed under reduced pressure and column chromatography (silica gel, EtOAc/Hexane, 25:75) of the residue afforded the title compound as an oil (1.80 g, 71%)

Workup

  1. temperatureat reflux for 3 h
  2. customAfter quenching with water and extraction with EtOAc
  3. extractionthe organic extract
  4. washwas washed with H2O, brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure and column chromatography (silica gel, EtOAc/Hexane, 25:75) of the residue

Sources & evidence

ORD record
ord-e716ee1c88a949eb86c2d4ca13e98406
Source dataset
uspto-grants-2000_01
Patent number
US06017952

Reaction notes

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