Sodium Carbonate → HCID 11212036, compound

HRID 2298307Notes

Reaction equation

HRID 2298307 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+].[CH:28]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)([CH3:30])[CH3:29]>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>[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([C:2]2[C:6](=[O:7])[C:5]3([CH2:11][CH2:10][CH2:9][CH2:8]3)[O:4][C:3]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:33][CH:32]=1)([CH3:30])[CH3:29]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27734804-Isopropylphenylboronic acidHCID 18386004HCID 18386004, compound

Product 1

HCID 11212036HCID 11212036, compoundYield 74.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 3-bromo-2-(4-methylsulfonylphenyl)-1-oxa-spiro[4,4]non-2-en-4-one (105 mg) in 5 ml of toluene and 15 ml ethanol, were added 20 mg of tetrakis(triphenylphosphine)palladium(0), 5 ml of 2 M aqueous sodium carbonate solution, and 50 mg of 4-isopropylbenzeneboronic acid. The reaction solution was stirred at 90° C. for 12 hours. The solvent was removed under reduced pressure and the resulting residue was extracted with 20 ml water and dichloromethane (30 ml×3). The organic layer was concentrated in vacuo and the resulting crude product was purified by column chromatography (hexane/ethylacetate) to obtain 87 mg of 3-(4-isopropyl-phenyl)-2-{4-(methylsulfonyl)phenyl}-1-oxa-spiro[4,4]non-2-en-4-one as a solid. mp: 139-140° C. NMR: δ1.25 (s, 3H), 1.27 (s, 3H), 2.04 (m, 6H), 2.15 (m, 2H), 2.92 (m, 1H), 3.06 (s, 3H), 7.21 (m, 4H), 7.83 (d, J=8.7 Hz, 2H), 7.93 (d, J=8.7 Hz, 2H). IR (cm−1): 2960, 1694, 1622, 1386, 1318, 1161, 768.

Workup

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

Sources & evidence

ORD record
ord-f068c1d30c694d5a93a0bf8c17fc71ef
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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