ChemicalBook CAS DataBase List (S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran

(S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran synthesis

11synthesis methods

Product Name:(S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran
CAS Number:915095-94-2
Molecular formula:C17H16ClIO2
Molecular Weight:414.67

(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran can be used as a reactant/reagent for the preparation of C-aryl D-glutofuranoside compounds, which can As a reference compound for glipizide quality control. (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran can be synthesized by using oxalyl dichloride as the starting material through three-step reaction.

915095-87-3 Synthesis

(2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone

915095-87-3
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(S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran

915095-94-2
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Yield:915095-94-2 90%

Reaction Conditions:

with aluminum (III) chloride;sodium tetrahydroborate in tetrahydrofuran for 5 h;Reflux;

Steps:

3
Equipped with a thermometer, a reflux condenser, a 500 mL three-necked flask with a drying tube was added VI (50g, 116.5mmol), THF (350mL), stirring at room temperature was added NaBH₄(22.0g, 582.5mmol), was added portionwise AlCl₃(39g, 291.5mmol), with vigorous bubbling system, the addition was complete the reaction was heated at reflux for 5 h, TLC detection starting material the reaction was complete, the reaction was stopped.A system was cooled to room temperature and slowly poured into 200mL ice water + 75mL 2MHCl stirred vigorously for 0.5h, allowed to stand separated and the aqueous phase was extracted with ethyl acetate (100mL × 3). The combined organic phases were washed with sodium bicarbonate solution until neutral, saturated sodium chloride (200 mL) washed, dried and concentrated to give the crude product as a pale yellow solid, water was added 50mL + 10mL of ethanol as a white solid crystallized to give 26.6g IV of them, in 90% yield.

References:

Shanghai Institute of Technology;Pan, Xianhua;ZHANG, XIN;ZHANG, RONG;Cao, Yang;CHEN, YANYU;LI, HONGYI;PENG, QIUJUN CN105399735, 2016, A Location in patent:Paragraph 0043; 0044; 0045

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