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CAS No. : | 16807-30-0 | MDL No. : | MFCD22627905 |
Formula : | C9H12O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 200.25 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
3.5% | Stage #1: N-chloro-succinimide; 3,4,5-trimethoxyphenylmercaptan In dichloromethane at -78 - 0℃; for 0.25h; Stage #2: methyl 5-methoxyindole-2-carboxylate In dichloromethane at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4% | Stage #1: 3,4,5-trimethoxyphenylmercaptan With N-chloro-succinimide In dichloromethane at -78 - 0℃; for 0.25h; Stage #2: ethyl 5-methoxy-1H-indole-2-carboxylate In dichloromethane at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; 1,2-dichloro-ethane; | EXAMPLE 85A 3,4,5-trimethoxybenzenethiol A room temperature suspension of zinc powder (430 mg, 6.56 mmol) and dichlorodimethylsilane (0.80 mL, 6.59 mmol) in 1,2-dichloroethane (15 mL) was treated with a solution of <strong>[39614-62-5]3,4,5-trimethoxybenzenesulfonyl chloride</strong> (500 mg, 1.87 mmol) and 1,3-dimethyl-2-imidazolidinone (647 mg, 5.67 mmol) in 1,2-dichloroethane (15 mL). The reaction was heated to 75 C. for 1 hour, cooled to room temperature, filtered, and concentrated. The concentrate was dissolved in methanol, concentrated, dissolved in methanol, and concentrated. The concentrate was purified by flash column chromatography on silica gel with dichloromethane to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With oxygen; sodium iodide In dimethyl sulfoxide at 120℃; for 16h; Schlenk technique; Green chemistry; regioselective reaction; | |
60% | With manganese(IV) oxide; iodine; oxygen at 120℃; for 48h; Schlenk technique; | |
3.5% | Stage #1: 3,4,5-trimethoxyphenylmercaptan With N-chloro-succinimide In dichloromethane at -78 - 0℃; for 0.25h; Stage #2: methyl 5-methoxyindole-2-carboxylate In dichloromethane at 0℃; for 1h; | 11 To a solution cooled to -78 °C of N-chlorosuccinimide (0.68 g, 0.0051 mol) in anhydrous dichloromethane (40 mL) was added 3,4,5- trimethoxybenzenethiol (33) (1.02 g, 0.0051 mol). Compound 33 prepared according to procedure in Offer, J.; Boddy, C. N. C; Dawson, P. E. Extending synthetic access to proteins with a removable acyl transfer auxiliary. J. Am. Chem. Soc. 2002, 124, 4642-4646. The reaction was warmed to 0 °C over 15 min, and a solution of methyl 5- methoxyindole-2-carboxylate (26) (0.87 g, 0.00424 mol) in anhydrous EPO dichloromethane (16 HiL) was added. The reaction was stirred at 0 °C for 1 h and then concentrated under reduced pressure. The residue was suspended in water (24 niL) and stirred for 1 h. The mixture was extracted with ethyl acetate; the organic layer was washed with brine and dried. Removal of the solvent furnished a crude product that was purified on a silica gel column (ethyl acetate-«-hexane 1 :2) to afford 21, yield 3.5 %, mp 123-128 0C (from ethanol). 1H NMR (CDCl3): δ 3.68 (s, 6H), 3.74 (s, 3H)3 3.78 (s, 3H), 3.94 (s, 3H), 6.48 (s, 2H)5 6.92 (d, J = 2.40 Hz, IH), 7.01 (dd, J = 8.92 and 2.45 Hz, IH), 7.32 (d, J = 8.93 Hz, IH), 9.16 ppm (broad s, IH, disappeared on treatment with D2O). IR (nujol): 3293, 1683 cm"1. Anal. Calcd. (C20H21NO6S (403.46)) C, H, N, S. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In toluene; at 110℃; for 29h;Inert atmosphere; | Into a round bottomed flask under an inert atmosphere of N2 was placed t-NaOBu (176 mg, 1.831 mmol), CuI (23 mg, 0.122 mmol), neocuproine (25 mg, 0.122 mmol), thiol 8 (269mg, 1.343 mmol) and iodide 10 (340 mg, 1.221 mmol) dissolved in anhydrous toluene (37 mL). The reaction mixture was heated for 29 h at 110 oC and then cooled to room temperature, filtered, and the formed solid was washed with toluene. The solvent was removed under reduced pressure, and the product was purified by preparative thin layer chromatography on silica gel 60 eluted with hexane/EtOAc 7:3 to give pure compound 2 (124 mg, 0.353 mmol). Yield 29 %. |