Triethylamine → HCID 12051603, compound

HRID 2085333Notes

Reaction equation

HRID 2085333 reaction equation
CS(Cl)(=O)=O.C([CH:8]1[C:12](O)([C:13]([OH:15])=[O:14])[C:11]2[C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH2:20][C:10]=2[O:9]1)C.[CH2:23](N(CC)CC)[CH3:24].[OH-].[Na+]>ClCCl>[O:22]=[C:17]1[C:11]2[C:12]([C:13]([O:15][CH2:23][CH3:24])=[O:14])=[CH:8][O:9][C:10]=2[CH2:20][CH:19]([CH3:21])[CH2:18]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 22730904HCID 22730904, compound

Product 1

HCID 12051603HCID 12051603, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (6.1 ml, 78.5 mmol) in dichloromethane (50 mL) was added to a stirring solution of ethyl 3-hydroxy 4-oxo-6-methyl-2,3,4,5,6,7-hexahydrobenzofuran-3-carboxylic acid (18.48 g, 76 mmol) and triethylamine (21.4 mL, 154 mmol) in dichloromethane (150 mL) at 0° C. The mixture was allowed to reach ambient temperature, stirred for 2 hours, then poured into aqueous 1N sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give ethyl 4-oxo-6-methyl-4,5,6,7-tetrahydrobenzofuran-3-carboxylate (16.86 g).

Workup

  1. customto reach ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-867c6911fd284be0b5d5a51537f9d755
Source dataset
uspto-grants-2004_04
Patent number
US06720339B2

Reaction notes

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