ChemicalBook CAS DataBase List (S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate synthesis

9synthesis methods

Product Name:(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate
CAS Number:1000414-38-9
Molecular formula:C11H12O4
Molecular Weight:208.21

69716-04-7 Synthesis

2-(6-HYDROXY-1-BENZOFURAN-3-YL) ACETIC ACID

69716-04-7
107 suppliers
$19.00/1g

124-41-4 Synthesis

124-41-4
684 suppliers
$12.00/25g

(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

1000414-38-9
68 suppliers
$72.00/100mg

Yield:1000414-38-9 89%

Reaction Conditions:

Stage #1: 2-(6-hydroxy-1-benzofuran-3-yl)acetic acid;sodium methylatewith bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate;(+)-1,1-bis[(2R,4R)-2,4-diethylphosphotano]ferrocene;hydrogen in methanol at 20; for 2 h;Inert atmosphere;
Stage #2: with sulfuric acid in methanol; for 4 h;Reflux;

Steps:

YZ-6 Preparation of YZ-6

Weigh bis(1,5(cyclooctadiene)rhodium trifluoromethanesulfonate (94mg, 0 2mmol), (-)-1,1-bis((2S,4S)-2,4-diethylphosphono)ferrocene (88mg, 0.2mmol), was dissolved in 30mL of methanol, stirred at room temperature under an argon atmosphere and fell another 15 minutes Weigh YZ-5 (4g, 21mmol) and MeONa (540mg, 10mmol. ) was dissolved in 70mL of methanol, and stirred at room temperature under gas gas protection. the first configured catalyst in methanol was added to the reaction solution at .7MPa hydrogen pressure, stirred at room temperature for 2 hours until the reaction was complete the reaction. the resultant concentrate was filtered the filtrate of the reduction product, the crude product was dissolved in methanol 100mL, 10mL added concentrated sulfuric acid was refluxed for about 4 hours, until the reaction was complete the reaction was cooled to room temperature, concentrated, dissolved in 200mL ethyl acetate, washed with water, saturated sodium bicarbonate solution , saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude product was purified by flash column chromatography (20% ethyl acetate / petroleum ether) to afford the product YZ-6 (3. 9g), two-step total yield 89%, ee value of 91.8%.

References:

CN103145663,2016,B Location in patent:Paragraph 0119-0121