Sulfuric Acid → Tert-butyl 5-oxotetrahydrofuran-2-carboxylate

HRID 1032035Notes

Reaction equation

HRID 1032035 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.[CH2:15]=[C:16]([CH3:18])[CH3:17].C(=O)([O-])O.[Na+]>ClCCl>[O:1]=[C:2]1[O:6][CH:5]([C:7]([O:9][C:16]([CH3:18])([CH3:17])[CH3:15])=[O:8])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 2515245-Oxo-2-tetrahydrofurancarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 15097814Tert-butyl 5-oxotetrahydrofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g of 5-oxo-2-tetrahydrofurancarboxylic acid in 100 ml of dichloromethane was added 0.3 ml of concentrated sulfuric acid, to which was further added an excess volume (ca. 50 ml) of isobutene. The reaction mixture was left standing overnight at room temperature under tight sealing, which was poured into a cooled saturated aqueous solution of sodium hydrogencarbonate. The dichloromethane layer was separated, washed with water, dried (Na2SO4) and concentrated to give t-butyl 5-oxo-2-tetrahydrofurancarboxylate as a colorless oily substance.

Workup

  1. waitThe reaction mixture was left
  2. customThe dichloromethane layer was separated
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-58d1299c31724502925b0511d8366162
Source dataset
uspto-grants-1990_09
Patent number
US04956358

Reaction notes

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