Water → HCID 14835580, compound

HRID 1709979Notes

Reaction equation

HRID 1709979 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]=[C:9]([C:17]([O:19]CC)=[O:18])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Na].O>O1CCOCC1>[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:17]([OH:19])=[O:18])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 14835579HCID 14835579, compound

Product 1

HCID 14835580HCID 14835580, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 9 (5 g, 17.2 mmoles) was dissolved in dioxane (11.5 ml) and a solution of sodium hydroxyde (11.5 ml, 1.5M) was added. The mixture was heated for 2 hours and poured in ice cooled water. The aqueous layer was extracted at pH 12 with Et2O (50 ml), acidified to pH 2 and reextrated with EtOAc (100 ml). This layer was dried (MgSO4), filtered and evaporated to give yellow crystals (4.2 g, 90%), after recrystallization (cyclohexane/CCl4) mp 176° C. 1H NMR (CDCl3) δ=1.25 (3H, t, J=7 Hz) 2.9 (2H, t) 3.5-3.9 (2H, m) 4.2 (2H, q, J=7 Hz) 7-7.6 (4H, m) 7.8 (1H, s). IR (CCl4) 3500-3000 (large signal) 3000 (w) 1695 (s) 1630 (w) 1600 (w) 1575 (w) 1490 (w) 1450 (w) 1410 (m) 1385 (w) 1370 (2) 1340 (w) 1320 (m). Mass spectrum m/z 261.

Workup

  1. temperatureThe mixture was heated for 2 hours
  2. additionpoured in ice
  3. extractionThe aqueous layer was extracted at pH 12 with Et2O (50 ml)
  4. dry with materialThis layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5672f2bc3cf2467ba3738651d3ff45af
Source dataset
uspto-grants-1990_08
Patent number
US04952573

Reaction notes

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