Isobutylene → Tert-butyl 5-oxotetrahydrofuran-2-carboxylate

HRID 2352286Notes

Reaction equation

HRID 2352286 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3]1.[CH2:10]=[C:11]([CH3:13])[CH3:12].C(=O)(O)[O-].[Na+]>ClCCl>[O:1]=[C:2]1[O:6][CH:5]([C:7]([O:9][C:11]([CH3:13])([CH3:12])[CH3:10])=[O:8])[CH2:4][CH2:3]1

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of 5.0 g 5-oxo-2-tetrahydrofurancarboxylic acid in 100 ml dichloromethane 0.3 ml concentrated sulfuric acid and then an excess amount of isobutene (about 50 ml) were added, while maintaining the solution at -60° C. The reaction mixture was kept standing in a tightly seald flask at room temperature overnight, and thereafter it was poured into a cooled saturated aqueous solution of sodium bicarbonate, and the dichloromethane layer was separated. After washing with water and drying (over Na2SO4), the dichloromethane layer was concentrated to yield t-butyl 5-oxo-2- tetrahydrofurancarboxylate in the form of a colorless oily substance.

Workup

  1. customthe dichloromethane layer was separated
  2. washAfter washing with water
  3. dry with materialdrying (over Na2SO4)
  4. concentrationthe dichloromethane layer was concentrated

Sources & evidence

ORD record
ord-d1b5bacca95141caa4bd2f7240c0b267
Source dataset
uspto-grants-1989_10
Patent number
US04876251

Reaction notes

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