A Facile Syntheses of (Z)-2-Phenoxy(THIO)methylene-γ-pentanolide and (Z)-2-Phenoxy(THIO)methyl-2-penten-γ- lactone

Abstract

Abstract: Starting from 3 phenoxy(thio) 1 propyne 1a(1b), 5 phenoxy(thio)₃ pentyn 2 ol 2a(2b) were obtained by Grignard reaction. After treating 2a(2b) with Jones reagent, hydroiodination of 3a(3b) with a reagent system of TMSCl/NaI/H₂O in CH 3CN, the conjugated product (Z) 5 phenoxy(thio) 4 iodo 3 pentene 2 one 4a(4b) and de conjugated product (Z) 5 phenoxy(thio) 4 iodo 3 pentene 2 one 5a(5b) were generated. In the presence of Pd(PPh₃)₄, Et 3N, and CO in toluene, the intramolecular cyclization of reducing products of 4a(4b) and 5a(5b) afforded the target compounds (Z)₂ phenoxy(thio) methylene γ pentanolide 9a(9b) and (Z)₂ phenoxy(thio) methyl 2 penten γ lactone 8a(8b) respectively in good yields. All compounds have been fully characterized by ¹H and ¹³CNMR, IR and MS spectroscopy. The one pot deconjugation and hydroiodination of 3a(3b) with a reagent system of TMSCl/NaI/H₂O in CH₃CN was the key step.

Key words: Hydroiodination, &gamma, Pentenolide, Synthesis, Deconjugation

CLC Number:

O622.6

TrendMD:

LIU Li Jun, LUO Fen Tair. A Facile Syntheses of (Z)-2-Phenoxy(THIO)methylene-γ-pentanolide and (Z)-2-Phenoxy(THIO)methyl-2-penten-γ- lactone[J]. Chem. J. Chinese Universities, 2003, 24(4): 632.

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A Facile Syntheses of (Z)-2-Phenoxy(THIO)methylene-γ-pentanolide and (Z)-2-Phenoxy(THIO)methyl-2-penten-γ- lactone

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