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

HRID 2393838Notes

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% Et2 O-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% Et2 O-hexanes)

Sources & evidence

ORD record: ord-702d87562aa2470fbaca5ddbb85aa33c
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808083

Reaction notes

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