2,6-Di-tert-butyl-4-methylphenol → HCID 19710197, compound

HRID 725927Notes

Reaction equation

HRID 725927 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:10]2)(=O)=O.[CH2:25]([Sn](CCCC)(CCCC)C#C)[CH2:26]CC.[Cl-].[Li+].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.[F-].N1C=CC=CC=1>C(OCC)C.N1C=CC=CC=1>[C:25]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:10]2)#[CH:26]

Participants

8

Reactant 5

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 621176EthynyltributyltinHCID 19710221HCID 19710221, compoundHCID 22468310HCID 22468310, compound

Product 1

HCID 19710197HCID 19710197, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-trifluoromethanesulfonyloxy-2-(di-n-propylamino)indan (Example 2) in 1,4-dixoane is treated with tri-n-butylethynylstannane, lithium chloride, tetrakis(triphenylphosphlne)palladium(0), and a few crystals of 2,6-di-tert-butyl-4-methylphenol under nitrogen (J. Am. Chem. Soc. 1987, 109, 5478). The mixture is refluxed for 6 h, cooled to room temperature, and treated with pyridine and pyridine fluoride and iluted with diethyl ether. The resulting crude product is purified by chromatography to give the title compound.

Workup

  1. temperatureThe mixture is refluxed for 6 h
  2. customThe resulting crude product is purified by chromatography

Sources & evidence

ORD record
ord-8a0ee0b2273545a9bad4e13a2ffb1522
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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