Hydrochloric Acid → HCID 14852935, compound

HRID 1534095Notes

Reaction equation

HRID 1534095 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[CH:15])[CH:5]=[CH:4][C:3]1=2.[CH3:17][S:18]([C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1)(=[O:20])=[O:19].C(N(CC)CC)C.Cl>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:24]3[CH:25]=[CH:26][C:21]([S:18]([CH3:17])(=[O:20])=[O:19])=[CH:22][CH:23]=3)[CH:5]=[CH:4][C:3]1=2

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 147265491,1,4,4-Tetramethyl-6-ethynyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 14852935HCID 14852935, compoundYield 117.2%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.2 g (0.015 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetylene, 3 g (0.0128 mol) of 4-methylsulfonylbromobenzene, 12.7 g (0.126 mol) of triethylamine, 12.3 mg (0.047 mmol) of triphenylphosphine, 1.9 mg (0.0027 mmol) of bis(triphenylphosphine)palladium(II) chloride and 6.5 mg (0.034 mmol) of copper(I) iodide in 4 ml of dry dimethylformamide were refluxed under nitrogen. After the reaction was complete, the cooled mixture was poured into water, and the mixture was adjusted to pH 5 with dilute hydrochloric acid and extracted with ether. The organic phase was washed with water, dried over sodium sulfate and evaporated to give 5.5 g of a residue which was recrystallized from methanol to provide 3.5 g of the title compound. Melting point: 153°-155° C.

Workup

  1. extractionextracted with ether
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-5bec40458c6f4d97b2ed3264a33ca933
Source dataset
uspto-grants-1992_02
Patent number
US05087637

Reaction notes

Loading…