Diethyl Ether → HCID 15289611, compound

HRID 342016Notes

Reaction equation

HRID 342016 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:15])[CH2:13][C:12](=[O:14])[O:11][C:9]1=[O:10].[C:16](C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].[N+](=C)=[N-].CCOCC.[NH4+].[Cl-]>C1COCC1.C(O)(=O)C>[CH3:7][C:8]([CH3:15])([CH2:9][OH:10])[CH2:13][C:12]([O:11][CH3:16])=[O:14]

Participants

9

Reactant 6

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 25517Ammonium ChlorideHCID 870672,2-Dimethylsuccinic anhydrideHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15289611HCID 15289611, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a suspension of LAH (lithium aluminum hydride) (4.9 g, 0.129 mol) in THF (300 mL) maintained at -78° C. was added during 45 min a solution of 2,2-dimethylsuccinic anhydride (16.5 g, 0.129 mol) in THF (350 mL). After 45 min of vigourous stirring the reaction mixture was warmed to -60° C. and pourred into 1M aqueous sodium potassium tartrate (500 mL) and stirred for 2 h at r.t. The mixture was then acidified with acetic acid (150 mL) and extracted three times with EtOAc. The combined organic phases were washed with brine and dried over Na2SO4. The residual oil was dissolved in ether and a solution of diazomethane in ether (about 300 mL, 0.15 mol) was added until the yellow color remained. An aqueous solution of NH4Cl was added and the ester was extracted with EtOAc and dried over MgSO4. The oil was purified by flash chromatography with 2:3 EtOAc:hexane to yield the title compound (13.5 g, 72%).

Workup

  1. temperaturewas warmed to -60° C.
  2. stirringstirred for 2 h at r.t
  3. extractionextracted three times with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. dissolutionThe residual oil was dissolved in ether
  7. extractionthe ester was extracted with EtOAc
  8. dry with materialdried over MgSO4
  9. customThe oil was purified by flash chromatography with 2:3 EtOAc

Sources & evidence

ORD record
ord-461d3240a5ca49dab006561d751bed42
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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