ChemicalBook CAS DataBase List (6-HYDROXY-BENZOFURAN-3-YL)-ACETIC ACID METHYL ESTER

(6-HYDROXY-BENZOFURAN-3-YL)-ACETIC ACID METHYL ESTER synthesis

6synthesis methods

Product Name:(6-HYDROXY-BENZOFURAN-3-YL)-ACETIC ACID METHYL ESTER
CAS Number:726174-52-3
Molecular formula:C11H10O4
Molecular Weight:206.19

67-56-1 Synthesis

67-56-1
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69716-04-7 Synthesis

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

69716-04-7
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(6-HYDROXY-BENZOFURAN-3-YL)-ACETIC ACID METHYL ESTER

726174-52-3
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Yield: 100%

Reaction Conditions:

with sulfuric acid in water at 60;

Steps:

348.1 Step 1:
To a solution of 2-(6-hydroxy-1-benzofuran-3-yl) acetic acid (2.00 g, 10.4 mmol) in methanol (11.0 mL) was added conc sulfuric acid (1.2 mL). The reaction mixture was stirred at 60 °C overnight. Analysis by tlc/LCMS indicated consumption of the starting material and formation of the amine product ([M+lj = 207.09). The reaction mixture was cooled to rt, then carefully quenched by the addition of iN NaOH (to pH 6-7) and extracted with EtOAc (3 x). The organic layers were combined,washed with brine, dried (over Na2504), filtered then concentrated in vacuo to afford methyl 2-(6- hydroxybenzofuran-3-yl)acetate (2.15 g, quant), which was immediately processed in the subsequent step.

References:

GILEAD SCIENCES, INC.;AKTOUDIANAKIS, Evangelos;APPLEBY, Todd;CHO, Aesop;DU, Zhimin;GRAUPE, Michael;GUERRERO, Juan A.;JABRI, Salman Y.;LAD, Lateshkumar Thakorlal;MACHICAO TELLO, Paulo A.;MEDLEY, Jonathan William;METOBO, Samuel E.;MUKHERJEE, Prasenjit Kumar;NADUTHAMBI, Devan;NOTTE, Gregory;PARKHILL, Eric Q.;PHILLIPS, Barton W.;SIMONOVICH, Scott Preston;SQUIRES, Neil H.;VENKATARAMANI, Chandrasekar;WANG, Peiyuan;WATKINS, William J.;XU, Jie;YANG, Kin Shing;ZIEBENHAUS, Christopher Allen WO2018/195321, 2018, A1 Location in patent:Page/Page column 509