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CAS No. : | 135145-34-5 | MDL No. : | MFCD08458908 |
Formula : | C8H9ClO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QYUQVBHGBPRDKN-LURJTMIESA-N |
M.W : | 156.61 | Pubchem ID : | 6950741 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
49% | With C45H32I4O6; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at -30℃; for 2h; | The racemic alcohol (1s) at -30 C1.0 mmol as a catalyst was dissolved in 5 ml dichloromethane (wherein, R I andn is 2; and pharmaceutically acceptable salts thereof) compound of the formula(2) the addition of 0.01 mol% of potassium and fluoro one equivalent offluoride, a carboxylic acid group and the ion exchange resin 80 mg silylatingagent of formula (5), including (in the formula, R is methyl) wasadded to 0.7 equivalents, and then the mixture was stirred for 1 hour. Filteringthe mixture was concentrated and then to recover the potassium fluoride and theion exchange resin. The residue was purified by flash chromatography (acetone /hexane / triethylamine = 1: 5: 0.025) to give the chiral alcohol; to give the(2s, 46% yield 97% ee, (S) -form). |
46% | With potassium fluoride; C46H34I4O6; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at -30℃; | At -30C, racemic alcohol (1s) 1.0 mmol was dissolved in 5 ml dichloromethane, the compound of formula 2(wherein, R is I and n is 2; and pharmaceutically acceptable salts) 0.01 mol% as a catalyst and the addition of 0.7 eq., of silylating agent formula (5) (in the formula, R4 is methyl)and 1 equivalent of potassium fluoride and 80 mg of carboxylic acid group ion exchange resin was added and stirred for 1 hour. The mixture was filtered then concentrated to recover potassium fluoride and the ion exchange resin. The residue was purified by flash chromatography (acetone /hexane / triethylamine = 1: 5: 0.025) to give the chiral alcohol (2s, 46% yield 97% ee, (S)-form). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Racemic secondary alcohols (0.25 mmol), catalyst (1.5 mol% of substrate), and KBr (0.02 mmol, 0.0024 g) were added to H2O(1.5 mL). The mixture was stirred for 10 min at room temperature, and then PhI(OAc)2 (0.175 mmol, 0.056 g) was added in four equal parts. The reaction progress was monitored by gas chromatography (GC). After achieving the desired oxidation level, the reaction mixture was heated to 40 ?C. The catalyst was precipitated out of the reaction system, washed with diethyl ether(3× 5 mL), dried in a vacuum, and finally recharged with fresh substrate, additive, and oxidant for the next catalytic cycle. The supernatants separated from the reaction system were extractedwith ether three times. The collected organic phase was driedover sodium sulfate and concentrated in a vacuum. The resultantmixture was purified by column chromatography on silica gel athe stationary phase (petroleum ether/ethyl acetate, 90/10). Enantioselectivitywas determined by a Agilent Technologies 6890NGC system equipped with a 19091G-B213 chiral capillary column(30 m×0.32 mm×0.25 m) with an FID. |
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