2,6-Lutidine → HCID 18993077, compound

HRID 375635Notes

Reaction equation

HRID 375635 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1.N1C(C)=CC=CC=1C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:1][CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 12543487Ethyl 5-(hydroxymethyl)furan-2-carboxylate

Product 1

HCID 18993077HCID 18993077, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 5-hydroxymethyl-2-carboethoxyfuran (2.94 g, 17.3 mmol), prepared as in step 1, in CH2Cl2 (50 mL) was added 2,6-lutidine (2.50 mL, 21.5 mmol) and methanesulfonyl chloride (1.50 mL, 19.0 mmol). The reaction mixture was stirred for 40 min at 0° C., then the cold bath was removed and stirring was continued for 2 hours. The reaction mixture was extracted with 1N aqueous HCl and saturated aqueous NaHCO3, and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-methanesulfonyloxymethyl-2-carboethoxyfuran (4.0 g) as a yellow oil which was used without further purification.

Workup

  1. customthe cold bath was removed
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. extractionThe reaction mixture was extracted with 1N aqueous HCl and saturated aqueous NaHCO3
  5. dry with materialthe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-167a3b83373c4a7fa6b1e59df3d5e89d
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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