Ammonia → HCID 20526841, compound

HRID 67277

Reaction equation

HRID 67277 reaction equation
[NH2-].[Li+].[Li].N.[CH3:5][O:6][CH:7]([O:15][CH3:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[CH:14].C[O:18][CH:19](OC)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]I>CS(C)=O>[CH3:16][O:15][CH:7]([O:6][CH3:5])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=[O:18]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 24532Lithium amideHCID 3028194LithiumHCID 205268401,1-Dimethoxy-6-iodohexaneHCID 205268491,1-Dimethoxy-oct-7-yne

Product 1

HCID 20526841HCID 20526841, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred suspension of lithium amide, prepared from 1.45 g (0.21 atom) of lithium in ca. 200 ml of liquid ammonia was added 30.6 g (0.18 Mole) of 1,1-dimethoxy-oct-7-yne over a period of 10 min. Dimethyl-sulfoxide (100 ml) was then added, followed by 62.5 g (0.23 Mole) of 1,1-dimethoxy-6-iodohexane within 10 min. Work-up as above gave an oil, from which low-boiling impurities were removed by heating at 100°/0.05 Torr. Crude tetradec-7-yn-1,14-dial dimethylacetal (40.8 g, 72% yield) was used without further purification. A sample was submitted to a rapid distillation: b.p. 140°/0.05 Torr.--IR: 1125, 1070, 1050 cm-1.

Workup

  1. customabove gave an oil
  2. customfrom which low-boiling impurities were removed
  3. temperatureby heating at 100°/0.05 Torr

Sources & evidence

ORD record
ord-87f56a3cfd314d67914e508a925488f4
Source dataset
uspto-grants-1982_08
Patent number
US04346023

Linked notes

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