Water → HCID 69492820, compound

HRID 396585Notes

Reaction equation

HRID 396585 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)=[O:15])[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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>[CH3:11][O:10][C:6]1[CH:5]=[C:4]([CH:12]=[CH:13][C:14]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)=[O:15])[CH:3]=[C:2]([C:29]2[S:28][CH:32]=[CH:31][CH:30]=2)[C:7]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 69620911HCID 69620911, compound

Product 1

HCID 69492820HCID 69492820, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-(3-Bromo-4,5-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (0.105 g, 0.2 mmol) from Ex-1A was dissolved in ethylene glycol dimethyl ether (20 mL). Tetrakis(triphenylphosphine)palladium(0) (0.116 g, 0.1 mmol) was added, and the mixture was stirred at room temperature under nitrogen for 5 min. 2-Thiopheneboronic acid (0.128 g) and sodium carbonate solution (2 M, 0.5 mL) were added. The mixture was stirred at reflux under nitrogen overnight. Upon cooling to room temperature it was poured into water (100 mL) and extracted with dichloromethane (100 mL). The organic phase was dried over sodium sulfate and evaporated. Silica gel chromatography (hexane/ethyl acetate, 4:1, 2:1) gave 0.079 g (90%) of the desired 3-[3,4-dimethoxy-5-(thien-2-yl)phenyl]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one product as a slightly yellow residue. 1H-NMR (300 MHz, CDCl3): 7.79 (d, 1H), 7.56 (m, 2H), 7.42 (d, 1H), 7.39 (d, 1H), 7.29 (s, 2H), 7.10-7.16 (m, 2H), 3.89-4.00 (m, 15H). Anal. Calculated for C24H24O6S C: 65.44, H: 5.49, S: 7.28; found C: 65.69, H: 5.59, S: 6.99.

Workup

  1. stirringThe mixture was stirred
  2. temperatureat reflux under nitrogen overnight
  3. temperatureUpon cooling to room temperature it
  4. extractionextracted with dichloromethane (100 mL)
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-dede5fbf73a44763aef93df4038a302d
Source dataset
uspto-grants-2003_08
Patent number
US06608101B1

Reaction notes

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