1-BENZOFURAN-6-OL

The benzofuranyl carbonyl moiety was prepared by protecting the hydroxyl groupof compound 13 by reacting with tert-butyldimethylsilyl chloride (1.0 equivalents) andtriethylamine (TEA, 1.1 equivalents) in acetone, to give compound 14 in 79percent yield. A solutionof compound 14 in methanol was then treated with sodium borohydride (1.0 equivalent) at roomtemperature overnight. The reaction was quenched with an addition of acetone, stirred at roomtemperature for a further 2.5 hours, aqueous HC1 (4N) was added with the temperature controlledto below 28 °C, tetrahydrofuran (THF) was added, and the solution stirred overnight under argonand in the absence of light. The product, compound 15, was isolated quantitatively by extractioninto methylene chloride, concentrated at low heat, and used without further purification. Thetriflate ester, compound 16, was produced in 69percent yield from compound 15 by reacting it with Nphenyl-bis(trifluoromethanesulfonimide) (1.0 equivalent) in methylene chloride for 72 hours.Compound 16 in a mixture of DMF, methanol, and triethylamine, was added to a preparedsolution of palladium acetate, 1, 3-Bis(diphenylphosphino)propane (dppp), DMF and methanol inan autoclave. Carbon monoxide was charged into the autoclave to a pressure of 8 bar, and the reaction mixture was heated at 70 °C for 6 hours. After workup, compound 17 was isolated in 91percent yield. Lithium hydroxide (4 equivalents) in methanol and water was used to hydrolyze the ester and permit the isolation of compound 18' in 97percent yield.

Molecular Weight:134.13
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:134.036779430
Monoisotopic Mass:134.036779430
Topological Polar Surface Area:33.4
Heavy Atom Count:10
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes