Structure of 71998-70-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 71998-70-4 |
Formula : | C11H16O3 |
M.W : | 196.24 |
SMILES Code : | OCCC(O)COCC1=CC=CC=C1 |
MDL No. : | MFCD11846119 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With copper(l) iodide; methyllithium; In diethyl ether; at -40 - 0℃; for 3h;Inert atmosphere; | To a stirred suspension of CuI (14.7 g, 74.2 mmol) in anhydrous Et2O (147 mL) at 0 C was added slowly MeLi (92.7 mL, 0.148 mmol, 1.6 M in Et2O) under an N2 atm, and the resulting solution was stirred for 15 min at 0 C. Epoxy alcohol 16 (4.8 g, 24.7 mmol) in anhydrous Et2O (20 mL) was then added dropwise at -40 C. Once the addition was complete, the mixture was stirred at 0 C for 3 h. The reaction was quenched by the careful addition of sat. aq NH4Cl solution. The mixture was filtered through a pad of Celite, and the salts were washed several times with Et2O. The combined organic layers were washed with brine (2 × 20 mL) and dried over Na2SO4. Concentration of the Et2O extract under reduced pressure provided 4.9 g (23.4 mmol, 94%) of a pale yellow oil, which was a 6:1 mixture of the regioisomeric diols. This mixture was dissolved in THF (60 mL) and treated with H2O (30 mL) containing NaIO4 (7.4 g, 34.7 mmol) with stirring to cleave the 1,2-diol. The reaction was complete in 1 h. After the layers were separated, the aq layer was extracted with Et2O (3 × 30 mL) and the combined extracts dried over Na2SO4 and concentrated in vacuo. The residue was subjected to silica gel column chromatography (EtOAc-hexane, 4:6) to afford diol 17 (3.5 g, 69%) as a pale yellow liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen; In tetrahydrofuran; at 140℃; under 38002.6 Torr; for 4h;Autoclave; | In a glove box, into a 125 mL autoclave was charged with ruthenium complex 1a (8.7 mg, 0.0143 mmol),potassium tert-butoxide (1.6 mg, 0.0143 mmol), tetrahydrofuran (20 mL) and 4-benzyloxymethyl-1,3-dioxan-2-one (5.94g, 28.6 mmol). The autoclave was sealed, removed from the glove box, and filled with hydrogen gas to 50 atm. Thereaction vessel was heated in an oil bath at 140C with stir for 4 hours. The reaction vessel was cooled in an ice-waterbath for 1.5 hours, and the excess of hydrogen was slowly deflated. The yield of methanol was determined as 99% withp-xylene as internal standard by using gas chromatography. The separation yield of the diol is 97%. |