Oxalic Acid → HCID 23311336, compound

HRID 746054Notes

Reaction equation

HRID 746054 reaction equation
[O:1]=[C:2]1[C:6]([CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]2[CH2:19][CH:20]=[CH:21][CH:22]=[C:4]2[O:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>C1COCC1.CCOCC.C(Cl)Cl>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[CH3:18][N:16]([CH3:17])[CH2:15][CH2:14][CH2:13][C:6]([C:5]1[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=1[OH:3])([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:2][OH:1]

Participants

7

Reactant 3

HCID 971Oxalic AcidHCID 21226445Aluminium lithium hydrideHCID 54040486HCID 54040486, compound

Product 1

HCID 23311336HCID 23311336, compoundYield 52.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(2-oxo-3-phenyl-3-dihydrobenzofuranyl)-N,N-dimethylpropylamine (103 g, 349 mmol) in anhydrous THF (400 ml) was added to a suspension of LiAlH4 (15.3 g, 384 mmol) in Et2O (300 ml) at ice bath temperature and this mixture stirred for 2 hours. After further stirring 1 hour at room temperature the reaction mixture was quenched with saturated Na2SO4, filtered and the solids washed with EtOAc (4×500 ml). The combined organic phases were washed with saturated Na2CO3 (500 ml) and saturated NaCl (500 ml), and dried over Na2SO4. Filtration and evaporation gave 66 g of a crude oil which solidified on standing. A solution of 40 g of this material in CH2Cl2 (60 ml) was added to a stirred solution of anhydrous oxalic acid (19 g) in anhydrous Et2O (600 ml). Filtration of the precipitated salt gave 43 g of a solid. Recrystallization of the oxalate (6.0 g) from boiling EtOH (300 ml) yielded 4.3 g (38%) of crystals, m.p. 182.0°-182.5°.

Workup

  1. stirringAfter further stirring 1 hour at room temperature the reaction mixture
  2. customwas quenched with saturated Na2SO4
  3. filtrationfiltered
  4. washthe solids washed with EtOAc (4×500 ml)
  5. washThe combined organic phases were washed with saturated Na2CO3 (500 ml) and saturated NaCl (500 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and evaporation
  8. customgave 66 g of a crude oil which
  9. filtrationFiltration of the precipitated salt

Sources & evidence

ORD record
ord-c4b7b7d0a8394fc9bad6d2ab40d094bf
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

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