Methanol → HCID 66679578, compound

HRID 1019679Notes

Reaction equation

HRID 1019679 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5]2.CCN(CC)CC.[CH3:22][OH:23].CN([CH:27]=[O:28])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>[CH3:22][O:23][C:27]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5]2)=[O:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 162276996-Bromo-2H-1-benzopyran-3-carboxylic acid

Product 1

HCID 66679578HCID 66679578, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of XXXI (2 g, 7.84 mmol), Pd (PPh3)4 (1.36 g, 1.18 mmol), Et3N (3.3 mL, 23.52 mmol), MeOH (30 mL) and DMF (10 mL) was heated at 80° C. for 12 h under carbon monoxide atmosphere. After solvent removal, the residue was extracted with EtOAc and the organic phase was washed with brine, dried over Na2SO4, filtered, and evaporated. After silica gel column purification, 1.2 g of 2H-chromene-3,6-dicarboxylic acid 6-methyl ester XXXII was obtained (Yield 66%). MS: calc'd 235 (MH+), exp 235 (MH+).

Workup

  1. customAfter solvent removal
  2. extractionthe residue was extracted with EtOAc
  3. washthe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customAfter silica gel column purification

Sources & evidence

ORD record
ord-7b90075a91e442f09578b35790f4c4c3
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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