2-Methyl-3-butyn-2-ol → HCID 20481568, compound

HRID 1648722Notes

Reaction equation

HRID 1648722 reaction equation
I[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH3:16][C:17]([OH:21])([CH3:20])[C:18]#[CH:19].P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Pd].[Cu]I.C(N(CC)CC)C>[OH:21][C:17]([CH3:20])([CH3:16])[C:18]#[C:19][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 11776TriphenylphosphineHCID 10757956HCID 10757956, compound

Product 1

HCID 20481568HCID 20481568, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

To 142 g (0.45 mole) of 1-(4'-iodophenoxy)-2-diethylaminoethane, 1.2 liters of triethylamine and 37.8 g (0.45 mole) of 3-methyl-1-butin-3-ol are added, under nitrogen, 3.4 g of the palladium complex PdCl2 [P(C6H5)3 ]2 and 1.9 g of copper(I) iodide. After the exothermic reaction has subsided, the reaction mixture is stirred for 15 hours at room temperature, then filtered, and the solution is evaporated in vacuo to dryness. The oily residue crystallises immediately. The product is dried in vacuo at 40° C., affording 123 g (99%) of 1-(3-hydroxy-3-methyl-1-butyn-1-yl)-4-(2-diethylaminoethoxy)benzene with a melting point of 64° C.

Workup

  1. customAfter the exothermic reaction
  2. filtrationfiltered
  3. customthe solution is evaporated in vacuo to dryness
  4. customThe oily residue crystallises immediately
  5. customThe product is dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-d1d264575a6347048634997002fe44aa
Source dataset
uspto-grants-1983_11
Patent number
US04412856

Reaction notes

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