Iodoethane → HCID 66831765, compound

HRID 58540Notes

Reaction equation

HRID 58540 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6]1.I[CH2:16][CH3:17]>CN(C=O)C>[CH2:16]([O:3][CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6]1)[CH3:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 23643400Ethyl 5-(hydroxymethyl)-4,5-dihydro-1,2-oxazole-3-carboxylate

Product 1

HCID 66831765HCID 66831765, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.141 g; 3.51 mmol) was added to a solution of ethyl 5-(hydroxymethyl)-4,5-dihydroisoxazole-3-carboxylate (0.338 g; 1.76 mmol) in DMF (3 mL) in an ice bath. The mixture was stirred for 10 min before addition of iodoethane (0.430 mL; 5.27 mmol). The ice bath was removed and the mixture was stirred at room temperature for 2 h. After evaporation, the residue was partitioned between brine and dichloromethane and the solution extracted with dichloromethane. Organic extracts were evaporated and the residue was purified by flash chromatography on silica gel (eluent: 1-6% ethyl acetate in dichloromethane) to afford 0.142 g (40%) of ethyl 5-(ethoxymethyl)-4,5-dihydroisoxazole-3-carboxylate.

Workup

  1. customThe ice bath was removed
  2. customAfter evaporation
  3. customthe residue was partitioned between brine and dichloromethane
  4. extractionthe solution extracted with dichloromethane
  5. customOrganic extracts were evaporated
  6. customthe residue was purified by flash chromatography on silica gel (eluent: 1-6% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-c02caa71ff834a129605d4fc49a44f1b
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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