Hydrochloric Acid → 4-[1-(Ethoxyimino)propyl]spiro[cyclohexane-1,1'indan]-3,5-dione

HRID 236246Notes

Reaction equation

HRID 236246 reaction equation
[C:1]([CH:5]1[C:18](=[O:19])[CH2:17][C:8]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)[CH2:7][C:6]1=[O:20])(=O)[CH2:2][CH3:3].Cl.[CH2:22]([O:24][NH2:25])[CH3:23].C([O-])(=O)C.[Na+].Cl>C(O)C>[CH2:22]([O:24][N:25]=[C:1]([CH:5]1[C:18](=[O:19])[CH2:17][C:8]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)[CH2:7][C:6]1=[O:20])[CH2:2][CH3:3])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 143486004-Propionylspiro[cyclohexane-1,1'-indan]-3,5-dione

Product 1

HCID 540008974-[1-(Ethoxyimino)propyl]spiro[cyclohexane-1,1'indan]-3,5-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Propionylspiro[cyclohexane-1,1'-indan]-3,5-dione (0.54 g), ethoxyamine hydrochloride (1.3 equiv), anhydrous sodium acetate (1.3 equiv) and absolute ethanol (20 ml) were stirred at room temperature for 3 hr. The mixture was poured into a very dilute aqueous hydrochloric acid solution which was then immediately extracted with diethyl ether. The dried (MgSO4) organic fraction was evaporated to give 4-[1-(ethoxyimino)propyl]spiro[cyclohexane-1,1'indan]-3,5-dione (5) as a pale yellow oil. Pmr spectrum (CDCl3 ; δ in ppm): 1.09-1.41 (6H, 2×t); 2.06 (2H, t); 2.6-3.1 (8H, m); 4.12 (2H, q); 7.2 (4H, m); 14.93 (1H, brs).

Workup

  1. extractionwas then immediately extracted with diethyl ether
  2. dry with materialThe dried (MgSO4) organic fraction
  3. customwas evaporated

Sources & evidence

ORD record
ord-e364554bad684a6990357369b3fbfaa9
Source dataset
uspto-grants-1987_02
Patent number
US04643763

Reaction notes

Loading…