Sodium Carbonate → HCID 59496794, compound

HRID 417057Notes

Reaction equation

HRID 417057 reaction equation
[CH:1]1([C:6]([C:8]2[CH:9]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:11]=[C:12]([OH:14])[CH:13]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:23]1[O:31][C:30]2[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][C:25]=2[O:24]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=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>[O:24]1[C:25]2[CH:26]=[CH:27][C:28]([C:10]3[CH:9]=[C:8]([C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[O:7])[CH:13]=[C:12]([OH:14])[CH:11]=3)=[CH:29][C:30]=2[O:31][CH2:23]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 59496823HCID 59496823, compound

Product 1

HCID 59496794HCID 59496794, compoundYield 36.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 3-cyclopentanecarbonyl-5-hydroxy-phenyl ester (300 mg) in 1,2-dimethoxyethane (4 mL) were added 3,4-methylenedioxyphenylboronic acid (295 mg), 2 M aq. sodium carbonate solution (0.9 mL) and Pd(PPh3)4 (10 mg) and the resulting mixture was stirred at 90° C. for 3 h. Then the reaction mixture was diluted with ethyl acetate, filtered through Celite and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 100 mg of the title compound (36% yield). HRMS calcd for C19H18O4 [M+H]+ 311.1278, observed 311.1277.

Workup

  1. filtrationfiltered through Celite
  2. washwashed with water and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-0776d7839de7426babb764c35662ded6
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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