Sodium Iodide → HCID 18436659, compound

HRID 456406Notes

Reaction equation

C([Si](OCCO[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Cl)(C)C)(C)(C)C.[I-].[Na+].[I-].C[C:22](=[O:25])[CH2:23][CH3:24]>>[CH2:15]([O:14]/[CH:13]=[CH:12]/[CH2:24][CH2:23][CH2:22][OH:25])[CH3:16]

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 6569Methyl Ethyl Ketone

HCID 30165Iodide Ion

HCID 18436663HCID 18436663, compound

Product 1

HCID 18436659HCID 18436659, compound

Procedure

tert-Butyl-{2-[2-(2-chloro-ethoxy)-ethoxy]-ethoxy}-dimethyl-silane was converted to the corresponding iodide by refluxing with 5 equiv of NaI in 2-butanone for 6 h. This was then alkynylated and deprotected by the same process described above to provide E-5-Ethoxy-pent-4-en-1-ol: 1H NMR (500 MHz) 4.02 (q, J=6.8, 2H, H2C(5″)); 3.74–3.70 (m, 2 H, HCO); 3.68–3.66 (m, 2H, HCO); 3.64–3.60 (m, 4H, HCO); 3.54 (t, J=7.3, 2H, H2CO)); 2.49 (t, J=6.3, 1H, OH); 2.41 (t, J 7.3, 2H, H2CO); 1.33 (t, J=7.3, 3H, H3C(6″)); 13C NMR (100 (M+NH4); 186.

Sources & evidence

ORD record: ord-023792da668641419d66648e0fa4201c
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186709B2

Reaction notes

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