Sulfuric Acid → HCID 14835579, compound

HRID 1709978Notes

Reaction equation

HRID 1709978 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10](O)[CH:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:8][CH2:7]1)=[O:5])[CH3:2].OS(O)(=O)=O>C1COCC1>[CH2:1]([O:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 14835578HCID 14835578, compound

Product 1

HCID 14835579HCID 14835579, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 8 (7 g, 22.8 mmoles) was dissolved in THF (100 ml) and refluxed in presence of H2SO4 (13 ml) for 2 hours. THF was evaporated and the residue was poured in ice cooled water, extracted with ether (100 ml). The organic layer was dried (MgSO4), and evaporated. The residue was chromatographed (silica gel: 120 g, eluent: CH2Cl2 /EtOAc (95/5)] to give a viscous liquid 9 (5.7 g, 87%). (Found: C; H; N . Calc. for C16H19NO4 : C 66.42; H 6.62; N 4.84). 1H NMR (CDCl3) δ=1.1-1.5 (6H, 2 overlapped t, J=7 Hz) 2.9 (2H, t) 3.6 (2H, t) 3.9-4.4 (4H, 2 overlapped q, J=7 Hz) 7-7.5 (4H, m) 7.5-7.7 (1H, m) IR (CCl4) 2990 (m) 2950-2870 (several bands, ) 1705 (s) 1635 (m) 1605 (w) 1495 (m) 1470 (w) 1450(m) 1410 (s) 1390 (s) 1370 (m) 1340 (w) 1320 (s). Mass spectrum m/z 289.

Workup

  1. customTHF was evaporated
  2. additionthe residue was poured in ice
  3. temperaturecooled water
  4. extractionextracted with ether (100 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed (silica gel

Sources & evidence

ORD record
ord-b7d227d0da484f3fb8ddad04ad8678dd
Source dataset
uspto-grants-1990_08
Patent number
US04952573

Reaction notes

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