Formaldehyde → HCID 11973862, compound

HRID 1032799Notes

Reaction equation

HRID 1032799 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]#[CH:10].C([Li])CCC.[CH2:16]=[O:17].[Cl-].[NH4+]>O1CCCC1>[CH2:16]([OH:17])[C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]#[CH:10]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 744001,9-DecadiyneHCID 178418339Butyllithium

Product 1

HCID 11973862HCID 11973862, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 13.42 g of deca-1,9-diyne in 300 ml of absolute tetrahydrofuran were added dropwise over one hour while stirring at -40° C. in an atmosphere of dry nitrogen, 59.4 ml of n-butyllithium solution. After stirring for another hour, during which time the mixture was allowed to warm to 0° C., 6.0 g of paraformaldehyde were added and then the mixture was heated to boil under reflux (TLC:petroleum ether/ether--3:2). When the reaction was finished, a saturated solution of ammonium chloride was added at room temperature. The mixture was extracted several times with ether, the combined extracts were dried over sodium sulfate and then evaporated under vacuum. The oily residue was purified by column chromatography with petroleum ether/ether (3:2) to give 8.27 g of the title compound in the form of a liquid which slowly solidified on storing in a refrigerator.

Workup

  1. temperaturethe mixture was heated
  2. extractionThe mixture was extracted several times with ether
  3. dry with materialthe combined extracts were dried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe oily residue was purified by column chromatography with petroleum ether/ether (3:2)

Sources & evidence

ORD record
ord-49208f3ff2664da6a6a93f94a6913bb1
Source dataset
uspto-grants-1990_09
Patent number
US04959391

Reaction notes

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