Sodium Bicarbonate → HCID 22987081, compound

HRID 987877Notes

Reaction equation

HRID 987877 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])[CH:7]=[CH:8][C:9]=1OS(C(F)(F)F)(=O)=O)[CH3:2].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29](OB(O)O)=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>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.C(COC)OC>[CH2:1]([O:3][C:4]1[CH:5]=[C:6](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])[CH:7]=[CH:8][C:9]=1[C:29]1[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=1)[CH3:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 147699944-Methoxyphenyl boric acidHCID 22987088HCID 22987088, compound

Product 1

HCID 22987081HCID 22987081, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 1.0 g (2.82 mmol) of methyl 3(E)-(3-ethoxy-4-trifluoromethanesulfonyloxyphenyl)acrylate, 0.47 g (3.10 mmol) of 4-methoxyphenylboric acid, 0.71 g (8.46 mmol) of sodium bicarbonate and 20 ml of dimethoxyethane is flushed three times with argon, 163 mg (0.14 mmol) of tetrakis(triphenylphosphine)palladium(0) are then added and the reaction is then allowed to continue for 15 hours at 80° C. Thereafter, the reaction mixture is cooled and is partitioned between ethyl acetate and water and the organic phase is washed with water and dried over magnesium sulfate, filtered and evaporated down. The residue is chromatographed over 100 g of silica gel using toluene/ethyl acetate (3:1). This gives methyl 3(E)-(2-ethoxy-4′-methoxybiphenyl-4-yl)acrylate.

Workup

  1. additionare then added
  2. temperatureThereafter, the reaction mixture is cooled
  3. customis partitioned between ethyl acetate and water
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated down
  8. customThe residue is chromatographed over 100 g of silica gel

Sources & evidence

ORD record
ord-95896febeba74412b8be24092f4522b7
Source dataset
uspto-grants-2003_10
Patent number
US06632909B2

Reaction notes

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