ChemicalBook CAS DataBase List (R)-4-Propyldihydrofuran-2(3H)-one

(R)-4-Propyldihydrofuran-2(3H)-one synthesis

5synthesis methods

Product Name:(R)-4-Propyldihydrofuran-2(3H)-one
CAS Number:63095-51-2
Molecular formula:C7H12O2
Molecular Weight:128.17

(R)-4-Propyldihydrofuran-2(3H)-one can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process. (R)-4-Propyldihydrofuran-2(3H)-one can be synthesized by (R)-2-((tert-butoxycarbonyl)methyl)pentanoic acid with dimethyl sulfide borane in tetrahydrofuran.

(R)-2-(2-(tert-butoxy)-2-oxoethyl)pentanoic acid

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63095-51-2
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Yield:63095-51-2 78%

Reaction Conditions:

Stage #1:(R)-2-((tert-butoxycarbonyl)methyl)pentanoic acid with dimethyl sulfide borane in tetrahydrofuran at 10 - 25; for 16 h;Cooling with ice;
Stage #2: with hydrogenchloride in water at 0 - 25; for 24 h;Temperature;

Steps:

4
The 165 g (R) -2- (2- (tert-butoxy) -2-oxoethyl) pentanoic acid (Compound 7a) was dissolved in 1L of tetrahydrofuran was added dropwise under ice-cooling 84mL 10mol / L borane two dimethyl sulfide, maintaining the temperature below 10 .Dropwise addition at room temperature (20 ~ 25 ) was stirred for 16 h.The reaction solution was cooled to 0 , 300mL18% hydrochloric acid was added dropwise.Continue addition was complete at room temperature (20 ~ 25 ) was stirred for 24 hours.The reaction solution was added 500mL of saturated sodium chloride, extracted with methyl tert-butyl ether (500mL × 3) used.Sulfate, filtered, concentrated, and the residue was distilled under reduced pressure to give 76 g of colorless liquid (R) -4- propyl-dihydrofuran -2 (3H) - one, (compound 8a, 110 / 18mmHg, 78% yield) .

References:

Shanghai Huaxingxi Pharmaceutical Technology Co., Ltd;Fan, Penggao;Rao, Weijun;Jiang, Rongying CN106008411, 2016, A Location in patent:Paragraph 0056; 0057; 0058; 0059; 0072-0075; 0088-0091

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21963-27-9 Synthesis