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ChemicalBook CAS DataBase List 2,3-DIHYDRO-1,4-BENZODIOXIN-5-YLMETHANOL
274910-19-9

2,3-DIHYDRO-1,4-BENZODIOXIN-5-YLMETHANOL synthesis

5synthesis methods
-

Yield:274910-19-9 99%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 18 h;

Steps:

(2,3-Dihydrobenzo[Z>] [l,4]dioxin-5-yl)methanol (20)

To a solution of 2,3-dihydrobenzo[￡][l,4]dioxine-5-carboxylic acid (5.00 g, 28.0 mmol) in THF (150 mL) at 0 °C was added lithium aluminium hydride (2.13 g, 56.0 mmol) in small portions. The reaction mixture was stirred at 0 °C for 10 min and stirred for a further 18 h at r.t. Water (150 mL) was added to the reaction mixture which was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure to obtain 20 as yellow oil (3.22 g, 99%). 1H NMR (CDC13) δ 6.87-6.79 (m, 3H), 4.66 (s, 2H), 4.32-4.30 (m, 2H), 4.28-4.25 (m, 2H), 2.19 (bs, 1H). Found: [M+H-18]=149.5

References:

WO2017/155909,2017,A1 Location in patent:Paragraph 0075

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