2-Furancarboxylic acid → Furan-2-carboxylic acid (ethylthio)carbonyloxymethyl ester

HRID 1609743Notes

Reaction equation

HRID 1609743 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].C([O-])(O)=O.[Na+].[C:14](=[O:21])([S:18][CH2:19][CH3:20])[O:15][CH2:16]I>O.ClCCCl>[C:14](=[O:21])([S:18][CH2:19][CH3:20])[O:15][CH2:16][O:7][C:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

6

Reactant 3

HCID 69192-Furancarboxylic acidHCID 516892Sodium BicarbonateHCID 11436522(Ethylsulfanyl)(iodomethoxy)methanone

Product 1

HCID 14800947Furan-2-carboxylic acid (ethylthio)carbonyloxymethyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

2-Furancarboxylic acid (5.6 g, 50 mmol) is added to a stirred solution of NaHCO3 (8.4 g, 100 mmol) and TBA HSO4 (17.0 g, 50 mmol) in H2O (100 mL) at room temperature. After stirring for 10 min 1,2-dichloroethane (100 mL) is added and the stirring continued for 30 min. 5b (12.5 g, 50 mmol) in 1,2-dichloroethane (25 mL) is added over 15 min. The mixture is stirred for 60 min at room temperature. The organic phase is separated, washed with H2O (50 mL), dried (MgSO4), and evaporated. The residue is stirred with Et2O (100 mL), insoluble material filtered off and washed with Et2O. The combined Et2O-phases are evaporated and the residue crystallized from ice-cold pentane to yield 8.5 g (74%) of 6mb, mp 37.2°-38.4° C.

Workup

  1. additionis added
  2. customThe organic phase is separated
  3. washwashed with H2O (50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. stirringThe residue is stirred with Et2O (100 mL), insoluble material
  7. filtrationfiltered off
  8. washwashed with Et2O
  9. customThe combined Et2O-phases are evaporated
  10. customthe residue crystallized from ice-cold pentane
  11. customto yield 8.5 g (74%) of 6mb, mp 37.2°-38.4° C.

Sources & evidence

ORD record
ord-767969c7d63e43bdb4c2835319ef87ea
Source dataset
uspto-grants-1995_03
Patent number
US05401868

Reaction notes

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