Carbon Tetrachloride → HCID 21392636, compound

HRID 461927Notes

Reaction equation

HRID 461927 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH2:5][CH2:6]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:30]>CCCCCC>[CH3:1][C:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH2:5][CH2:6][Cl:30]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 103744723-Hexyn-1-ol, 5,5-dimethyl-

Product 1

HCID 21392636HCID 21392636, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

This preparation illustrates further procedures for preparing alkynylamines. In this preparation 0.1 mole of 5,5-dimethylhex-3-yn-1-ol is mixed with 0.1 mole of triphenylphosphine in 40 ml. of carbon tetrachloride and then heated, under nitrogen, at 60° C for 4 hours. The mixture is then poured into 200 ml. of hexane, stirred, and then filtered and the filtrate concentrated by evaporation under vacuum. The concentrate is then chromatographed on silica gel eluting with 5% ethyl acetate-95% vol. hexane, affording 5,5-dimethylhex-3-yn-1-yl chloride. b. 0.069 Mole of 5,5-dimethylhex-3-yn-1-yl chloride is treated according to the procedures described in paragraph (b) of Preparation A, affording 1-azido-5,5-dimethylhex-3-yne. c. 0.069 Mole of 1-azido-5,5-dimethylhex-3-yne is treated according to the procedure described herein in paragraph (c) of Preparation A affording 1-amino-5,5-dimethylhex-3-yne.

Workup

  1. additionThe mixture is then poured into 200 ml
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated by evaporation under vacuum
  4. customThe concentrate is then chromatographed on silica gel eluting with 5% ethyl acetate-95% vol. hexane

Sources & evidence

ORD record
ord-fc800442e03842a4ba7d368cc7adc14f
Source dataset
uspto-grants-1977_12
Patent number
US04064257

Reaction notes

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