A facile, selective KF/Al2O3 mediated method for the deprotection of aryl silyl ethers and preparation of aryl SEM ethers

Tetrahedron Letters

Volumn 42, Issue 9, 2001, Pages 1611-1613

  Blass, Benjamin E ^a   Harris, Cheryl L ^a   Portlock, David E ^a  

^a PROCTER AND GAMBLE PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (TRIMETHYLSILYL)ETHOXYMETHYL; ACETIC ACID; ALUMINUM OXIDE; DIOXANE; METHYL GROUP; ORGANOSILICON DERIVATIVE; PHENOL DERIVATIVE; POTASSIUM FLUORIDE; SILANE DERIVATIVE; SOLVENT; TERT BUTYLDIMETHYLSILYL 4 BROMOPHENOL; TERT BUTYLDIPHENYLSILYL 4 BROMOPHENOL; TRIMETHYLSILYL 4 BROMOPHENOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS; TEMPERATURE;

EID: 0035951930     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)02259-0     Document Type: Article

References (12)

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9. TMS=trimethylsilyl, TBDMS=tert-butyldimethyl silyl, TBDPS=tert-butyldiphenyl silyl, SEM=2-(trimethylsilyl)ethoxy methyl.
10. 3 (40% wt. KF) is added. The reaction is stirred at room temperature for 4 hours, filtered and stripped to an oily solid. Chromatography with 3/1 hexane/ethyl acetate provided 17.5 mg of 4-bromophenol.
11. Removal of the aryl silyl ether was confirmed by analysis of mass spectral fragmentation patterns.
12. 3 (40% wt. KF) are dissolved/suspended in 5.0 ml of DME and 102 μL of SEM-Cl (96.2 mg, 0.56 mmol) is added. The reaction is then stirred 2 hours, filtered and stripped to yield 165 mg (94%) of the desired product. No further purification was required.