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

HRID 1394603Notes

Reaction equation

HRID 1394603 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]([C:22]1[S:26][C:25]2[CH:27]=[CH:28][CH:29]=[C:30](I)[C:24]=2[CH:23]=1)(=[O:21])[CH3:20].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:19]([C:22]1[S:26][C:25]2[CH:27]=[CH:28][CH:29]=[C:30]([C:6]3[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=3[O:16][CH2:17][CH3:18])[C:24]=2[CH:23]=1)(=[O:21])[CH3:20]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 179527062-Acetyl-4-iodo benzo[b]thiopheneHCID 18504242(2-Ethoxy-3,5-diisopropylphenyl)-boronic acid

Product 1

HCID 179527472-Acetyl-4-(2-ethoxy-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-ethoxy 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-ethoxy-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-fbc94cba539c41fd93bad8dedf7f22af
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

Loading…