Sodium Carbonate → HCID 67296304, compound

HRID 2276853Notes

Reaction equation

HRID 2276853 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10](OB(O)O)=[CH:9][CH:8]=1)[CH3:2].Br[C:19]1[CH2:23][CH2:22][C:21](=[O:24])[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C:19]2[CH2:23][CH2:22][C:21](=[O:24])[CH:20]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5569412-Cyclopenten-1-one, 3-bromo-HCID 67296279HCID 67296279, compound

Product 1

HCID 67296304HCID 67296304, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

{4-[(2-Ethoxy-2-oxoethyl)thio]phenyl}boric acid 2.80 g (11.7 mmol) and 3-bromo-2-cyclopenten-1-one 1.88 g (11.7 mmol) synthesized according to the method of C. M. Marson et al. were dissolved in 25 mL of 1,2-dimethoxyethane, followed by addition of 12 mL of 3N aqueous sodium carbonate solution and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) methylene chloride complex 0.48 g (0.59 mmol), and the mixture was stirred for 4 hours at 90° C. The temperature of the reaction solution was adjusted to room temperature, followed by concentration. Then, water was added to the residue, followed by extraction with methylene chloride and drying over anhydrous magnesium sulfate. The solvent was concentrated, and the crude product obtained was purified by silica gel column chromatography (Biotage, solvent for elution; hexane/ethyl acetate) to give the title compound 2.43 g (yield 75%).

Workup

  1. customwas adjusted to room temperature
  2. concentrationfollowed by concentration
  3. additionThen, water was added to the residue
  4. extractionfollowed by extraction with methylene chloride
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated
  7. customthe crude product obtained
  8. customwas purified by silica gel column chromatography (Biotage, solvent for elution; hexane/ethyl acetate)

Sources & evidence

ORD record
ord-eedd3bb9bbe54d57bbfefbfa9665db78
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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