2-Methyl-3-butyn-2-ol → HCID 131716781, compound

HRID 981366Notes

Reaction equation

HRID 981366 reaction equation
Br[C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:11]([F:13])([F:12])[C:10]([F:15])([F:14])[C:9]([F:17])([F:16])[C:8]=2[O:18][C:19]2[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.[CH3:28][C:29]([OH:33])([C:31]#[CH:32])[CH3:30]>[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[OH:33][C:29]([CH3:30])([C:31]#[C:32][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:8]2[C:9]([F:17])([F:16])[C:10]([F:14])([F:15])[C:11]([F:12])([F:13])[C:7]=2[O:6][C:5]2[CH:26]=[CH:27][C:2]([C:32]#[C:31][C:29]([CH3:30])([OH:33])[CH3:28])=[CH:3][CH:4]=2)=[CH:24][CH:23]=1)[CH3:28]

Participants

6

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 14618029HCID 14618029, compound

Product 1

HCID 131716781HCID 131716781, compoundYield 48.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

39 g (0.075 mol) of 1,2-bis-(4-bromophenoxy)-3,3,4,4,5,5-hexafluorocyclopent-1-ene (obtained according to Example 1), 32 g (0.38 mol) of 2-methyl-3-butin-2-ol, 211 mg of PdCl2 (PPh3)2, 230 mg of CuI and 630 mg of triphenylphosphine were added under nitrogen to 100 ml of triethylamine. After heating to reflux for 24 hours, the reaction mixture was filtered and the filtrate was concentrated in vacuo. Recrystallization of the residue resulting here from n-hexane/ethyl acetate gave 19.1 g of product, which corresponds to 48% of theory, having a melting point of 108° to 113° C. The 1H NMR spectrum showed characteristic bands at 1.59 ppm, 6.63 ppm and 7.2 ppm, measured against tetramethylsilane as internal standard.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 24 hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customRecrystallization of the residue
  6. customresulting here from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-32615f90c4c841c4812ca01281b1e612
Source dataset
uspto-grants-1991_02
Patent number
US04990633

Reaction notes

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