Ethanol → HCID 17952735, compound

HRID 1394581Notes

Reaction equation

HRID 1394581 reaction equation
[C:1]([C:5]1[C:6]([O:18][CH2:19][CH3:20])=[C:7](B(O)O)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:21](=[O:24])([O-])[O-].[Na+].[Na+].O.[CH2:28]([OH:30])[CH3:29]>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:28]([C:21]1[O:24][C:10]2[C:9]([C:7]3[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=3[O:18][CH2:19][CH3:20])=[CH:8][CH:7]=[CH:6][C:5]=2[CH:1]=1)(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 17952702HCID 17952702, compound

Product 1

HCID 17952735HCID 17952735, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 300 mg (1.08 mmol) of 3,5-di-tert-butyl-2-ethoxy phenylboronic acid, 498 mg (1.62 mmol) of 2-acetyl-7-trifluoromethanesulfonate benzo[b]furan 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 395 mg (1.00 mmol, yield: 93%/boronic acid) of 2-acetyl-7-(3,5-di-tert-butyl-2-ethoxyphenyl)-benzo[b]furan as a clear yellow pasty solid. 1H NMR (CDCl3), δ: 7.72 (d, J=7.4 Hz, 1H), 7.68 (d, J=7.8 Hz, 1H), 7.56 (s, 1H), 7.42 (s, 2H), 7.38 (d, J=7.6 Hz, 1H), 3.35 (dd, J=13.9, 7.0 Hz, 2H), 2.58 (s, 3H), 1.48 (s, 9H), 1.36 (s, 9H), 0.86 (t, J=7.0 Hz, 3H).

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-436678e8a37d4bb5bef5ccf79384d2ad
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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