Hydrochloric Acid → 3-(DIPHENYLPHOSPHINO)PROPIONIC ACID

Diphenylphosphine (2.00 mL, 11.5 mmol) was dissolved in degassed CH3CN (20 mL). Methyl acrylate (3.80 mL, 42.5 mmol) and a few drops of benzyltrimethylammonium hydroxide (40 wt. % in MeOH) were added, and the resulting solution was stirred under Ar(g). The reaction was monitored by TLC and after the introduction of additional drops of base (after 2 h) the reaction was found to be complete after 4 h. The solution was then concentrated under reduced pressure; the resulting oil was dissolved in CH2Cl2 (100 mL) and concentrated again. The resulting oil was then dissolved in MeOH (10 mL) and an aqueous solution of KOH (4.00 g, 71.4 mmol in 10 mL of H2O) was added. The mixture was stirred under Ar(g). After 1 h, the reaction was found to be complete, and the solution was diluted with H2O (200 mL) and acidified to pH 2 with 2M HCl. The suspension was then extracted with CH2Cl2 (2×150 mL), and the organic layers were combined, dried over Na2SO4(s) and concentrated under reduced pressure. The solid residue was purified by silica gel flash chromatography, eluting with 2% MeOH/CH2Cl2, to give the acid 1d as a white solid (2.74 g, 10.6 mmol, 92% yield).

1. customafter the introduction of additional drops of base (after 2 h)
2. concentrationThe solution was then concentrated under reduced pressure
3. dissolutionthe resulting oil was dissolved in CH2Cl2 (100 mL)
4. concentrationconcentrated again
5. dissolutionThe resulting oil was then dissolved in MeOH (10 mL)
6. waitAfter 1 h
7. extractionThe suspension was then extracted with CH2Cl2 (2×150 mL)
8. dry with materialdried over Na2SO4(s)
9. concentrationconcentrated under reduced pressure
10. customThe solid residue was purified by silica gel flash chromatography
11. washeluting with 2% MeOH/CH2Cl2

ORDレコード

ord-c81563323e3e4f468a7ffb898e3d8c70

出典データセット

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08871916B2