Sodium Iodide → HCID 21932061, compound

HRID 1469877Notes

Reaction equation

HRID 1469877 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][CH2:8]1.[Na+].[I-:18]>CC(=O)CC.CCCCCCC>[I:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 21932004HCID 21932004, compound

Product 1

HCID 21932061HCID 21932061, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

To a solution of tert-butyl 1-(5-chloropentyl)-1-cyclopropanecarboxylate (31.5 g, 128 mmol) in 2-butanone (150 mL) was added NaI (24.9 g, 166 mmol). The reaction mixture was stirred under reflux for 24 h, diluted with heptane (220 mL) and filtered through a layer of silica (˜2 cm) in a glassfilter. The residue was eluted with a mixture of heptane and EtOAc (3:1, 5×100 mL). The combined filtrate and elutes were evaporated in vacuo to give tert-butyl 1-(5-iodopentyl)-1-cyclopropanecarboxylate (42.3 g, 99%) as a slightly yellow liquid. 1H NMR (CDCl3): δ=3.18 (t, J=7.1 Hz, 2H), 1.82 (quintet, J=7.1 Hz, 2H), 1.48-1.33 (m, 6H), 1.42 (s, 9H), 1.10 (dd, J=6.8 Hz, Hz, 2H), 0.58 (dd, J=6.6, 3.9 Hz, 2H). 13C NMR (CDCl3): δ=174.0, 79.9, 34.1, 33.6, 30.8, 28.2 (3×), 26.8, 24.3, 15.4 (2×), 7.4. HRMS calcd for C13H23IO2 (M+): 338.0743, found: 338.0743.

Workup

  1. temperatureunder reflux for 24 h
  2. filtrationfiltered through a layer of silica (˜2 cm) in a glassfilter
  3. washThe residue was eluted with a mixture of heptane and EtOAc (3:1, 5×100 mL)
  4. customThe combined filtrate and elutes were evaporated in vacuo

Sources & evidence

ORD record
ord-b5fe7af34945439795bb2076c0f76855
Source dataset
uspto-grants-2015_04
Patent number
US09006290B2

Reaction notes

Loading…