Sodium Carbonate → HCID 67031112, compound

HRID 2244468Notes

Reaction equation

HRID 2244468 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:16]1[CH:36]=[CH:35][C:19]([O:20][C@@H:21]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=1>C(COC)OC.O.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:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:16]1[CH:36]=[CH:35][C:19]([O:20][C@@H:21]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 67031076HCID 67031076, compound

Product 1

HCID 67031112HCID 67031112, compoundYield 120.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

0.024 mmol of tetrakis(triphenylphosphine)palladium, 12.3 mmol of 2-furanboronic acid and 7.5 ml of 2 M sodium carbonate solution are added to a solution of 6.15 mmol of ethyl (2S)-2-(4-bromophenoxy)-4-phenylbutanoate in 25 ml of dimethoxyethane. The mixture is refluxed for 2 hours. After cooling to room temperature, the mixture is taken up in water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate (Na2SO4) and then evaporated to dryness under vacuum. 2.6 g of a brown oil are obtained. This oil is chromatographed with a 9/1 heptane/ethyl acetate mixture as eluent. 1.5 g of an oil that crystallizes are obtained.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate (Na2SO4)
  4. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-025117a4d2c348b8bbee852b885b3cf7
Source dataset
uspto-grants-2010_03
Patent number
US07678831B2

Reaction notes

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