Triethylamine → HCID 21449437, compound

HRID 596961

Reaction equation

HRID 596961 reaction equation
[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7](Cl)=[O:8].[C:11]([CH:13]([OH:27])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)#[CH:12].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7]([O:27][CH:13]([C:11]#[CH:12])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 129190923-Phenoxy-alpha-ethynylbenzylalcohol

Product 1

HCID 21449437HCID 21449437, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,2,3,3-Tetramethylcyclopropanoyl chloride (3.05 g) was added with stirring to a solution of α-ethynyl-3-phenoxybenzylalcohol (4.8 g) and triethylamine (2.16 g) in dry toluene (70 ml) at 10° C. The solution was allowed to attain room temperature and stirred for 16 hours. The mixture was filtered and the solvent removed from the filtrate under reduced pressure. The residue was washed with 5% sulphuric acid, followed by saturated sodium bicarbonate solution and finally purified by chromatography on silica gel using toluene as eluent to give the desired product as an oil nD20 1.5455.

Workup

  1. customto attain room temperature
  2. filtrationThe mixture was filtered
  3. customthe solvent removed from the filtrate under reduced pressure
  4. washThe residue was washed with 5% sulphuric acid
  5. customfinally purified by chromatography on silica gel

Sources & evidence

ORD record
ord-62a9ecd109444ba88607cfac655e7ce0
Source dataset
uspto-grants-1977_03
Patent number
US04012522

Linked notes

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