Sodium Carbonate → HCID 11485472, compound

HRID 2298306Notes

Reaction equation

HRID 2298306 reaction equation
Br[C:2]1[C:6](=[O:7])[C:5]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[O:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>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>[CH3:21][S:18]([C:15]1[CH:16]=[CH:17][C:12]([C:3]2[O:4][C:5]3([CH2:11][CH2:10][CH2:9][CH2:8]3)[C:6](=[O:7])[C:2]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 18386004HCID 18386004, compound

Product 1

HCID 11485472HCID 11485472, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 3-bromo-2-(4-(methylsulfonyl)phenyl)-1-oxa-spiro[4,4]non-2-en-4-one (77 mg) in 5 ml of toluene and 15 ml ethanol, were added 15 mg of tetrakis(triphenylphosphine)palladium(0), 5 ml of 2 M aqueous sodium carbonate solution, and 27 mg of benzeneboronic acid. Then the reaction solution was stirred at 90° C. for 12 hours. The reaction solvent was evaporated off under reduced pressure and the resulting residue was extracted with 20 ml water and dichloromethane (30 ml×1). The organic layer was concentrated in vacuo and the resulting crude product mixture was purified by column chromatography (hexane/ethylacetate) to obtain 57 mg of 2-{4-(methylsulfonyl)phenyl}-3-phenyl-1-oxa-spiro[4,4]non-2-en-4-one as a solid. mp: 184-185° C. NMR: δ2.09 (m, 6H), 2.17 (m, 2H), 3.06 (s, 3H), 7.26 (m, 2H), 7,35 (m, 3H), 7.81 (d, J=8.1 Hz, 2H), 7.92 (d, J=8.1 Hz, 2H). IR (cm−1): 2925, 1695, 1591, 1403, 1150, 771.

Workup

  1. customThe reaction solvent was evaporated off under reduced pressure
  2. extractionthe resulting residue was extracted with 20 ml water and dichloromethane (30 ml×1)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe resulting crude product mixture was purified by column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-8be49b756dda457c99a07fc01840c7c4
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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