Water → HCID 22766917, compound

HRID 1283185Notes

Reaction equation

HRID 1283185 reaction equation
F[C:2](F)(F)C(O)=O.[N:8]1C=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14]([OH:19])(=O)[C:15](O)=[O:16].O.CS(C)=O.[CH:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CCOCC.CO>[CH3:2][C:14]1([CH:15]=[O:16])[C:9]2[NH:8][C:25]3[C:30]([C:10]=2[CH2:11][CH2:12][O:19]1)=[CH:29][CH:28]=[CH:27][CH:26]=3

Participants

8

Reactant 5

HCID 962WaterHCID 971Oxalic AcidHCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 18518713Benzene dimethylsulfoxide

Product 1

HCID 22766917HCID 22766917, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

N,N-dicyclohexylcarbodiimide (17.36 g, 0.084 mole) is added to a cooled, stirred solution of the above primary alcohol (6.09 g, 0.028 mole) in 63 ml of dimethyl sulfoxide-benzene (2:1) containing trifluoroacetic acid (1.12 ml, 0.014 mole) and pyridine (2.24 ml, 0.028 mole). The reaction is stirred at room temperature under nitrogen for 5 hr. The reaction mixture is now diluted with 600 ml of ether, followed by the dropwise addition of a solution of oxalic acid (7.56 g) in 21 ml of methanol. After 30 minutes, water (600 ml) is added and the insoluble material is collected. The organic phase is washed with water (2×), 5% aqueous sodium bicarbonate (2×) and water (2×). After drying (MgSO4) the organic phase is evaporated to yield an oil. The oil is purified by chromatography on silica gel. Elution with 10% ether in benzene affords the title compound as eluate, nmr (CDCl3) δ 1.59(s,3H), 2.84(t,J = 5.5 cps, 2H), 4.15(t, J = 5.5 cps, 2H).

Workup

  1. waitAfter 30 minutes
  2. customthe insoluble material is collected
  3. washThe organic phase is washed with water (2×), 5% aqueous sodium bicarbonate (2×) and water (2×)
  4. dry with materialAfter drying (MgSO4) the organic phase
  5. customis evaporated
  6. customto yield an oil
  7. customThe oil is purified by chromatography on silica gel
  8. washElution with 10% ether in benzene

Sources & evidence

ORD record
ord-60571732972b4d57b380677258b06bb8
Source dataset
uspto-grants-1976_08
Patent number
US03974179

Reaction notes

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