Sodium Iodide → HCID 23370044, compound

HRID 1900907Notes

Reaction equation

HRID 1900907 reaction equation
[H-].[Na+].[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[I-].[Na+].[CH2:20]([O:22][CH2:23][CH2:24]Cl)[CH3:21]>C(O)(C)(C)C>[C:14]([O:13][C:3]([CH:4]([CH2:21][CH2:20][O:22][CH2:23][CH3:24])[C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 24758Sodium hydrideHCID 68324Di-tert-butyl malonate

Product 1

HCID 23370044HCID 23370044, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A 55% dispersion of sodium hydride in mineral oil (5.46 g) was added by portions to a solution of di-t-butyl malonate (25.8 g) in t-butanol (100 ml) under argon. The reaction mixture was stirred at ambient temperature for 1 hour before sodium iodide (1.53 g) and 2-ethoxyethyl chloride (13.1 ml) were added. The resultant mixture was heated to reflux for 48 hours and then evaporated to dryness. The residue was partitioned between water and ether, the organic layer was separated, washed with brine, dried (MgSO4) and evaporated. The resultant oily residue was purified by flash chromatography on silica by elution with 10% ethyl acetate/hexane to give t-butyl 2-t-butoxycarbonyl-4-ethoxybutyrate (21 g) as a colourless oil: NMR Spectrum (CDCl3) 1.19 (3H, t), 1.45 (18H, s), 2.07 (2H, m), 3.34 (1H, t), 3.45 (4H, m); Mass Spectrum m/Z 289 (M+H)+.

Workup

  1. additionwere added
  2. temperatureto reflux for 48 hours
  3. customevaporated to dryness
  4. customThe residue was partitioned between water and ether
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe resultant oily residue was purified by flash chromatography on silica by elution with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8a227c86297d407697a8d5d057d5e558
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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