Ethanol → HCID 59682056, compound

HRID 1394579Notes

Reaction equation

HRID 1394579 reaction equation
[C:1]([C:4]1[O:8][C:7]2[C:9](Br)=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[CH2:14]([O:17][C:18]1[C:23]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:22][C:21]([CH2:28][CH3:29])=[CH:20][C:19]=1B(O)O)[CH2:15][CH3:16].C(O)C.C([O-])([O-])=O.[Na+].[Na+]>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:1]([C:4]1[O:8][C:7]2[C:9]([C:19]3[CH:20]=[C:21]([CH2:28][CH3:29])[CH:22]=[C:23]([C:24]([CH3:26])([CH3:25])[CH3:27])[C:18]=3[O:17][CH2:14][CH2:15][CH3:16])=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 179526991-(7-Bromo-1-benzofuran-2-yl)ethan-1-oneHCID 17952732HCID 17952732, compound

Product 1

HCID 59682056HCID 59682056, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 57 mg (0.049 mmol, 5%) of Pd(PPh3)4, 362 mg (1.26 mmol) of 2-acetyl-7-bromobenzo[b]furan and 2.52 mmol of 2-propoxy-3-tert-butyl-5-ethyl phenylboronic acid in 10 mL of toluene, and 5 mL of ethanol was added 1.3 mL of a 2N Na2CO3 aqueous solution. The mixture was heated to reflux for 3 hours and after cooling (room temperature) extracted with ethyl acetate. The organic layer was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was filtrated over a short silica plug (eluent: ethyl acetate/hexane: 10/90) and recrystallized from hexane to afford 2-acetyl-7-(2-propoxy-3-tert-butyl-5-ethylphenyl)benzo[b]furan as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvents were removed under reduced pressure
  6. filtrationThe crude product was filtrated over a short silica plug (eluent: ethyl acetate/hexane: 10/90)
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-e6671ad5373d484198d6d31e0cd49e70
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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