Isopropyl iodide → HCID 57949062, compound

HRID 1478164Notes

Reaction equation

HRID 1478164 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.I[CH:13]([CH3:15])[CH3:14]>CCOC(C)=O.[Ag-]=O>[CH:13]([O:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 6362Isopropyl iodideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 57949062HCID 57949062, compound

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1,4-dioxaspiro[4.5]decan-8-ol (0.5 g, 3.16 mmol) in 2-iodopropane (5.37 g, 31.6 mmol), silver (I) oxide (1.392 g, 6.01 mmol) was added and the reaction mixture was stirred at room temperature. Upon completion the resulting suspension was diluted with EtOAc and the suspension filtered under reduced pressure. The filtrate was concentrated under reduced pressure to give a pale yellow oil. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-30% EtOAc in iso-hexane to afforded the title compound;

Workup

  1. filtrationthe suspension filtered under reduced pressure
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto give a pale yellow oil
  4. customThe crude material was adsorbed onto silica and purification by chromatography
  5. washeluting with 0-30% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-aa89973df849466dbf15e7c55d48f196
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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