Ethyl orthoformate → 2-Pentadecynal diethylacetal

HRID 478014Notes

Reaction equation

HRID 478014 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH:15]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])OCC>[Zn+2].[I-].[I-]>[CH2:23]([O:22][CH:15]([O:19][CH2:20][CH3:21])[C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:24]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 698231-Tetradecyne

Product 1

HCID 141831442-Pentadecynal diethylacetal

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

1-Tetradecyne (100 g), (EtO)3CH (200 ml) and ZnI2 (15 g) were heated together (bath temperature 170°-175°) with distillative removal of ethanol (~90 minutes). The reaction mixture was evaporated in vacuo (bath temperature 80°) to remove excess (EtO)3CH. The residue was distributed between CH2Cl2 and water. The CH2Cl2 phase was separated, washed with aqueous NaHCO3, dried (Na2SO4) and evaporated in vacuo to provide a light brown oil. Yield: 135.4 g. This product was shown to be virtually pure by TLC and PMR and it was used as such in subsequent reactions.

Workup

  1. customwith distillative removal of ethanol (~90 minutes)
  2. customThe reaction mixture was evaporated in vacuo (bath temperature 80°)
  3. customto remove excess (EtO)3CH
  4. customThe CH2Cl2 phase was separated
  5. washwashed with aqueous NaHCO3
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customto provide a light brown oil

Sources & evidence

ORD record
ord-8f9bce379cf345aa97419ff2c87e4222
Source dataset
uspto-grants-1989_12
Patent number
US04889873

Reaction notes

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