Two mild and simple one-step desilylation-acetylations of a variety of alkyl- and aryl-trimethylsilyl ethers, Me3SiOR(Ar), with acetic anhydride in the presence of montmorillonite K-10 clay are described.
References
1.
TedderJ.M., NechvatalA., and JubbA. H., Basic Organic Chemistry; part V: Industrial products; Wiley, New York, 1975, pp. 569.
2.
HaslamE., Tetrahedron, 1980, 36, 2409 and references cited therein.
3.
LoupyA., PetitA., RamdaniM., and YvanaeffC., Can. J. Chem., 1993, 71, 90.
4.
OteraJ., Chem. Rev., 1993, 93, 1449 and references cited therein.
5.
BramG., LoupyA., and MajdoubM., Synth. Commun., 1990, 20, 125; G. Bram, A. Loupy, M. Majdoub, E. Gutierrez and E. Ruiz-Hitzky, Tetrahedron, 1990, 46, 5167.
6.
ZhdanovR.I., and ZhenodarovaS. M., Synthesis, 1975, 222.
7.
VedejsE., and DiverS. T., J. Am. Chem. Soc., 1993, 115, 3358.
8.
CopeA.C., and HerrickE. C., Org. Synth., 1963, Coll. 4, 304.
9.
VedejsE., BennettN. S., ConnL. M., DiverS. T., GingrasM., LinS., OliverP. A., and PetersonM. J., J. Org. Chem., 1993, 58, 7286,
10.
IqbalJ., and SrivastavaR. R., J. Org. Chem., 1992, 57, 2001.
11.
IshiharaK., KubotaM., KuriharaH., and YamamotoH., J. Org. Chem., 1996, 61, 4560.
12.
KnoevenagelE., Justus Liebigs Ann. Chem., 1914, 406, 133.
13.
BurwellR.L., Chem. Rev., 1954, 54, 615 and references cited therein.
14.
GanemB., and SmallV. R., J. Org. Chem., 1974, 39, 3728.
15.
KimS., and LeeW. J., Synth. Commun., 1986, 16, 659.
16.
LakourajM.M., MovassaghB., and FasihiJ., Synth. Commun., 2000, 30, 821.
17.
SummersL., J. Am. Chem. Soc., 1954, 76, 3481.
18.
ArakawaS., and HashimotoM., Bull. Chem. Soc. Jpn., 1968, 41, 1449.
