Water → 2-Acetyl-4-(2-n-butoxy-3,5-di-iso-propylphenyl)-benzo[b]thiophene

HRID 1394605Notes

Reaction equation

HRID 1394605 reaction equation
[CH:1]([C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:6](B(O)O)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[C:21]([C:24]1[S:28][C:27]2[CH:29]=[CH:30][CH:31]=[C:32](I)[C:26]=2[CH:25]=1)(=[O:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C.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:21]([C:24]1[S:28][C:27]2[CH:29]=[CH:30][CH:31]=[C:32]([C:6]3[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=3[O:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:26]=2[CH:25]=1)(=[O:23])[CH3:22]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 17952696(2-Butoxy-3,5-diisopropylphenyl)-boronic acidHCID 179527062-Acetyl-4-iodo benzo[b]thiophene

Product 1

HCID 179527972-Acetyl-4-(2-n-butoxy-3,5-di-iso-propylphenyl)-benzo[b]thiophene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1.08 mmol of 3,5-di-iso-propyl-2-n-butoxy phenylboronic acid, 1.62 mmol of 2-acetyl-4-iodo benzo[b]thiophene (see Example 14, 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-4-(2-n-butoxy-3,5-di-iso-propylphenyl)-benzo[b]thiophene.

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-3a7935b0b8134038b8dfaac0dd05161b
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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