Ethanol → HCID 86747815, compound

HRID 1033097Notes

Reaction equation

HRID 1033097 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[CH:10]=C(C(=O)CCl)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:35](O)(=[S:37])[CH3:36].[CH3:39][CH2:40]O>CCOCC>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[CH:10]=[C:36]([C:35](=[S:37])[CH2:39][CH3:40])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10796Cesium carbonateHCID 54257489HCID 54257489, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86747815HCID 86747815, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of chloroacetyl derivative from Step 3 (150 mg), Cs2CO3 (75 mg), thioacetic acid (30 μL) in EtOH (10 mL) was stirred at r.t. for 1 hr. The reaction mixture was diluted with Et2O, washed with pH 7 buffer solution, brine and the solvent evaporated. The residue was dissolved in MeOH, NaOMe (1M, 3 drops) and MeI (50 μL) was added. The mixture was stirred at r.t. for 3 hr. and diluted with a saturated NH4Cl solution and Et2O. The organic phase was separated, washed with H2O, brine, dried over MgSO4 and the solvent evaporated. The residue was flash chromatographed, eluting with hexane:EtOAc (85:15) to afford the title compound as a foam.

Workup

  1. washwashed with pH 7 buffer solution, brine
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in MeOH
  4. additionNaOMe (1M, 3 drops) and MeI (50 μL) was added
  5. stirringThe mixture was stirred at r.t. for 3 hr
  6. additionand diluted with a saturated NH4Cl solution and Et2O
  7. customThe organic phase was separated
  8. washwashed with H2O, brine
  9. dry with materialdried over MgSO4
  10. customthe solvent evaporated
  11. customchromatographed
  12. washeluting with hexane:EtOAc (85:15)

Sources & evidence

ORD record
ord-906433713f1641a880a2b44eb1c3cb03
Source dataset
uspto-grants-1994_05
Patent number
US05308852

Reaction notes

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