Propargyl alcohol → HCID 86667394, compound

HRID 2275983Notes

Reaction equation

HRID 2275983 reaction equation
[CH2:1](O)[C:2]#C.[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])#[N:6]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].CO>[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][C:1]#[CH:2])=[O:12])#[N:6]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 554130Methyl 5-cyanopentanoate

Product 1

HCID 86667394HCID 86667394, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

15.1 g (269 mmol) of propargyl alcohol and 1.92 g (7 mmol) of titanium tetraisopropoxide were added to 18.0 g of the obtained methyl 5-cyanovalerate, and heated and stirred at 120° C. for 8 hours while methanol was removed. After the reaction, methanol and excessive propargyl alcohol were evaporated away under reduced pressure, and the residue was purified through column chromatography (Wakogel C-200, elution with hexane/ethyl acetate=1/9) to give 16.7 g (yield 75%) of 2-propynyl 5-cyanovalerate.

Workup

  1. temperatureheated
  2. customwas removed
  3. customAfter the reaction, methanol and excessive propargyl alcohol
  4. customwere evaporated away under reduced pressure
  5. customthe residue was purified through column chromatography (Wakogel C-200, elution with hexane/ethyl acetate=1/9)

Sources & evidence

ORD record
ord-88a030d7006b401784b012d98be8018d
Source dataset
uspto-grants-2015_09
Patent number
US09130244B2

Reaction notes

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