Formaldehyde → 929-53-3

HRID 1463579Notes

Reaction equation

HRID 1463579 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH2:5]=[O:6].[CH2:7]1[CH2:11]O[CH2:9][CH2:8]1>>[CH:9]#[C:8][CH2:7][C:11]#[C:11][CH2:7][CH2:8][CH2:9][CH2:1][CH3:2].[CH2:5]([OH:6])[C:9]#[C:8][CH2:7][C:11]#[C:11][CH2:7][CH2:8][CH2:9][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 178418443HCID 178418443, compound

Product 2

HCID 11062440929-53-3HCID 111163932,5-undecadiyn-1-ol

Procedure

A solution of deca-1,4-diyne in THF was prepared following the method indicated in Example 1 and then an equivalent of ethylmagnesium bromide was added thereto at 0°. The mixture was kept at 60° for 45 min. After having added 1,2 equivalent of paraformaldehyde, the mixture was brought to reflux for 3 h. Once cooled, it was extracted with petroleum ether 80:100° and the organic phases were washed with water, then with an aqueous solution saturated with NaCl, dried and evaporated. The obtained residue was chromatographed on a column filled with silica, using as eluting agent a mixture of 1 to 10% of ethyl acetate in cyclohexane. Undeca-2,5-diyn-1-ol was thus obtained in 40% yield.

Workup

  1. customat 0°
  2. temperatureto reflux for 3 h
  3. temperatureOnce cooled
  4. extractionit was extracted with petroleum ether 80
  5. wash100° and the organic phases were washed with water
  6. dry with materialwith an aqueous solution saturated with NaCl, dried
  7. customevaporated
  8. customThe obtained residue was chromatographed on a column
  9. additionfilled with silica
  10. washas eluting agent
  11. additiona mixture of 1 to 10% of ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-f49d60ccd01e4267805676e1c0eb74fb
Source dataset
uspto-grants-1994_04
Patent number
US05300716

Reaction notes

Loading…