Formaldehyde → 1-Diethylamino-4(S)-acetyloxy-2nonyne

HRID 867112Notes

Reaction equation

HRID 867112 reaction equation
[C:1]([O:4][C@@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:6]#[CH:7])(=[O:3])[CH3:2].[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14].C=O.O1CCOC[CH2:21]1>CCOCC>[CH2:13]([N:15]([CH2:16][CH3:17])[CH2:21][C:7]#[C:6][C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:14]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 312751,4-DioxaneHCID 11829840(S)-oct-1-yn-3-yl acetate

Product 1

HCID 227938191-Diethylamino-4(S)-acetyloxy-2nonyneYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3(S)-acetyloxy-1-octyne (58.5 g., 0.35 mole), diethylamine (28.5 g., 0.39 mole), paraformaldehyde (13.8 g., 0.46 mole), and p-dioxane (60 ml.) is heated on the steam bath for 17 hours, then cooled to room temperature and diluted with ether (250 ml.). The resulting solution is extracted with 5% hydrochloric acid (300 ml.) providing an aqueous extract (acidic) which is made basic with 10% sodium hydroxide solution and extracted with ether. The organic extract is dried over sodium sulfate and filtered. In vacuo evaporation of the filtrate leaves a residual oil which is distilled to provide the title compound (73.1 g., 89%), b.p. 103°-109° C./0.3 mm.; [α]D26 -80° (C 3.3, CHCl3).

Workup

  1. temperatureis heated on the steam bath for 17 hours
  2. extractionThe resulting solution is extracted with 5% hydrochloric acid (300 ml.)
  3. customproviding
  4. extractionan aqueous extract (acidic) which
  5. extractionextracted with ether
  6. extractionThe organic extract
  7. dry with materialis dried over sodium sulfate
  8. filtrationfiltered
  9. customIn vacuo evaporation of the filtrate
  10. customleaves a residual oil which
  11. distillationis distilled

Sources & evidence

ORD record
ord-fc468295e9f74ae8a086a0d775b59d12
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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