| Identification | Back Directory | [Name]
Cyclohexanecarboxylic acid, 4-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-, ethyl ester | [CAS]
676560-15-9 | [Synonyms]
Ethyl 4-((tert-butyldiMethylsilyl)oxy)cyclohexanecarboxylate
Cyclohexanecarboxylic acid, 4-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-, ethyl ester | [Molecular Formula]
C15H30O3Si | [MOL File]
676560-15-9.mol | [Molecular Weight]
286.48 |
| Chemical Properties | Back Directory | [storage temp. ]
2-8°C | [InChI]
InChI=1S/C15H30O3Si/c1-7-17-14(16)12-8-10-13(11-9-12)18-19(5,6)15(2,3)4/h12-13H,7-11H2,1-6H3 | [InChIKey]
VFEJEBVELPDVHI-UHFFFAOYSA-N | [SMILES]
C1(C(OCC)=O)CCC(O[Si](C(C)(C)C)(C)C)CC1 |
| Hazard Information | Back Directory | [Synthesis]
A. Synthesis of ethyl 4-((tert-butyldimethylsilyl)oxy)cyclohexanecarboxylate. Under dry conditions, tert-butyldimethylchlorosilane (10.6 g, 70 mmol) and imidazole (9.9 g, 145 mmol) were dissolved in N,N-dimethylformamide (DMF, 20 mL). Subsequently, ethyl trans-4-hydroxycyclohexanecarboxylate (9.4 mL, 58 mmol) was added to this solution. The reaction mixture was stirred at 35 °C for 12 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (EtOAc, 100 mL) and washed with deionized water (3 × 100 mL). The organic phase was dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated to give the white solid product ethyl 4-((tert-butyldimethylsilyl)oxy)cyclohexanecarboxylate (16.6 g, quantitative yield). The product did not require further purification and could be used directly in subsequent steps. | [References]
[1] Patent: US2006/4039, 2006, A1. Location in patent: Page/Page column 13
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 129 - 134
[3] Patent: WO2009/9059, 2009, A1. Location in patent: Page/Page column 30
[4] Journal of Organic Chemistry, 1994, vol. 59, # 10, p. 2748 - 2761
[5] Patent: US2016/75711, 2016, A1. Location in patent: Paragraph 0219-0220 |
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