Acetone → HCID 54010765, compound

HRID 844002Notes

Reaction equation

HRID 844002 reaction equation
[CH:1](NC(C)C)(C)C.[Li].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([OH:16])=[O:15].[CH3:17][C:18]([CH3:20])=[O:19].C(O)(=O)C(O)=O>O1CCCC1.O>[CH3:1][O:15][C:14]([C:10]1[O:9][C:13]([C:18]([OH:19])([CH3:20])[CH3:17])=[CH:12][CH:11]=1)=[O:16]

Participants

8

Reactant 5

HCID 180AcetoneHCID 971Oxalic AcidHCID 69192-Furancarboxylic acidHCID 7912DiisopropylamineHCID 3028194Lithium

Product 1

HCID 54010765HCID 54010765, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (7.6 ml, 54.0 mmole) in tetrahydrofuran (20 ml) at 0° C. was added 2.5 M nButyl lithium (22 ml, 54.0 mmole). The mixture was cooled to −78° C. and a solution of Furan-2-carboxylic acid (3.0 grams, 27.0 mmole) in tetrahydrofuran (20 ml) was added dropwise and stirred for 20 minutes and acetone (2.4 ml, 32.0 mmole) was added. The mixture was stirred at −78° C. for 10 minutes and allowed to warm to room temperature over 1 hour. The mixture was poured into 200 ml water, acidified with oxalic acid to pH 2 and extracted with diethyl ether. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to give a solid. (0.580 g). MW 145.22; MS (m/e) 146 (M++1).

Workup

  1. stirringThe mixture was stirred at −78° C. for 10 minutes
  2. temperatureto warm to room temperature over 1 hour
  3. extractionextracted with diethyl ether
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a solid

Sources & evidence

ORD record
ord-b97ed59be34c4f38bafbde38da754830
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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