Ethanol → 2-Acetyl-7-(3,5-diisopropyl-2-ethoxyphenyl)-benzo[b]furan

HRID 1394583Notes

Reaction equation

HRID 1394583 reaction equation
[CH:1]([C:4]1[C:5]([O:16][CH2:17][CH3:18])=[C:6](B(O)O)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[C:19](=[O:22])([O-])[O-].[Na+].[Na+].O.[CH2:26]([OH:28])[CH3:27]>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>[C:26]([C:19]1[O:22][C:2]2[C:1]([C:4]3[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:6]([CH3:7])[CH3:5])[C:5]=3[O:16][CH2:17][CH3:18])=[CH:3][CH:9]=[CH:4][C:1]=2[CH:2]=1)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 18504242(2-Ethoxy-3,5-diisopropylphenyl)-boronic acid

Product 1

HCID 179527272-Acetyl-7-(3,5-diisopropyl-2-ethoxyphenyl)-benzo[b]furan

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1.08 mmol of 3,5-diisopropyl-2-ethoxy phenylboronic acid, 498 mg (1.62 mmol) of 2-acetyl-7-trifluoromethanesulfonate benzo[b]furan (see Example 4, step A) and 62 mg (0.05 mmol) of Pd(PPh3)4, 1 mL of 2N aqueous sodium carbonate in 9 mL of toluene and 4 mL ethanol was heated to reflux. After complexion (TLC), water was added and the solution was extracted with ethyl acetate. The organic layer is dried over MgSO4 and after evaporation of the solvents, the crude oil was purified over a short silica plug (eluent: 10/90=ethyl acetate/hexane) to afford 2-acetyl-7-(3,5-diisopropyl-2-ethoxyphenyl)-benzo[b]furan as a clear yellow pasty solid.

Workup

  1. temperaturewas heated to reflux
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer is dried over MgSO4
  4. customafter evaporation of the solvents
  5. customthe crude oil was purified over a short silica plug (eluent: 10/90=ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4072612b03494d02af118988242aa99b
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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