Water → Hex-5-yne 2-octylcycloprop-2-ene-1-carboxylate

HRID 840086Notes

Reaction equation

HRID 840086 reaction equation
[CH2:1]([C:9]1[CH:10]([C:12](Cl)=[O:13])[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[CH2:22]([OH:28])[CH2:23][CH2:24][CH2:25][C:26]#[CH:27].O>CCOCC>[CH2:1]([C:9]1[CH:10]([C:12]([OH:13])=[O:28])[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:27][CH2:26][CH2:25][CH2:24][C:23]#[CH:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 702345-Hexyn-1-olHCID 226216452-Octylcycloprop-2-ene-1-carbonyl chloride

Product 1

HCID 86583675Hex-5-yne 2-octylcycloprop-2-ene-1-carboxylateYield 9.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-octylcycloprop-2-ene-1-carbonyl chloride (330 mg, 1.5 mmol) in 5 ml of ether is added 1.5 ml of triethylamine. 5-Hexyn-1-ol (0.18 g, 1.8 mmol) was added to the reaction mixture, which was stirred at room temperature over the weekend. Water and additional ether were added, and the resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was washed with water and brine, dried over MgSO4, filtered and stripped. The product was chromatographed on silica gel to give 40 mg of 60% pure hex-5-yne 2-octylcycloprop-2-ene-1-carboxylate containing roughly 40% 2-octylcycloprop-2-ene-1-carboxylic acid.

Workup

  1. customthe resulting mixture was transferred to a separatory funnel
  2. customthe phases were separated
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe product was chromatographed on silica gel

Sources & evidence

ORD record
ord-61a8b821db6646c68a7ed29ae31f866d
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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