1-Pentyne → Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoate

HRID 277530Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]2[CH:9]=[C:10]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)[CH:11]=[CH:12][C:13]=2[C:14]([CH3:18])([CH3:17])[CH2:15][CH:16]=1)(=O)=O.[CH:34]#[C:35][CH2:36][CH2:37][CH3:38]>C(NCC)C.CCOC(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>[CH3:17][C:14]1([CH3:18])[C:13]2[CH:12]=[CH:11][C:10]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)=[CH:9][C:8]=2[C:7]([C:34]#[C:35][CH2:36][CH2:37][CH3:38])=[CH:16][CH2:15]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution (flushed with argon) of 201.3 mg (0.42 mmol) of ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-3-yl)ethynyl]benzoate (Compound 66), 286.5 mg (4.21 mmol) of 1-pentyne, 59.5 mg (0.08 mmol) of bis(triphenylphosphine)palladium(II) chloride and 32.0 mg (0.17 mmol) of cuprous iodide in 2.5 ml of diethylamine was heated to 70° C. in a pressure vial for 6 hours. After stirring overnight at room temperature, the mixture was diluted with EtOAc (25 ml) and washed with water and brine. The organic phase was dried over MgSO4, concentrated in vacuo and purified by column chromatography (silica, 5% Et2O-hexanes) to give the title compound as a colorless, air-sensitive oil.

Workup

washwashed with water and brine
dry with materialThe organic phase was dried over MgSO4
concentrationconcentrated in vacuo
custompurified by column chromatography (silica, 5% Et2O-hexanes)

Sources & evidence

ORD record: ord-ed748860f0554bec9bfe066c4fa28fdf
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355806B1

Reaction notes

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