Acetic Anhydride → Methyl 5-acetyl-3-methylfuran-2-carboxylate

HRID 2045955Notes

Reaction equation

HRID 2045955 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH3:6][O:7][C:8]([C:10]1[O:11][CH:12]=[CH:13][C:14]=1[CH3:15])=[O:9].[C:16](OC(=O)C)(=[O:18])[CH3:17].C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH3:6][O:7][C:8]([C:10]1[O:11][C:12]([C:16](=[O:18])[CH3:17])=[CH:13][C:14]=1[CH3:15])=[O:9]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 24287Tin tetrachlorideHCID 350231Methyl 3-methyl-2-furoate

Product 1

HCID 66587192Methyl 5-acetyl-3-methylfuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tin (IV) chloride (2.5 ml) is added to a solution of 3-methyl-furan-2-carboxylic acid methyl ester (1.0 g) and acetic anhydride (3.2 ml) in dichloromethane (8 ml) at 0° C. After 1 hour 30 minutes at 0° C. the reaction mixture is poured into a cold 10% Na2CO3 aqueous solution. The reaction mixture is filtered through a plug of Celite and the filtration cake is washed with dichloromethane. The aqueous phase is extracted two times with dichloromethane. The combined organic phases are washed once with water and with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-Acetyl-3-methyl-furan-2-carboxylic acid methyl ester (0.5 g) as a white solid. MS (HPLC/MS): 183 (MH+). Retention time: 1.09 min.

Workup

  1. filtrationThe reaction mixture is filtered through a plug of Celite
  2. washthe filtration cake is washed with dichloromethane
  3. extractionThe aqueous phase is extracted two times with dichloromethane
  4. washThe combined organic phases are washed once with water and with a saturated aqueous solution of NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-4525ce12a3cd4e8da16502633a59891c
Source dataset
uspto-grants-2013_11
Patent number
US08592418B2

Reaction notes

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