Tulipalin A synthesis
- Product Name:Tulipalin A
- CAS Number:547-65-9
- Molecular formula:C5H6O2
- Molecular Weight:98.1
![2(3H)-Furanone, 3-[(dimethylamino)methyl]dihydro-](/CAS/20210305/GIF/42023-17-6.gif)
42023-17-6
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547-65-9
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Yield:547-65-9 77% ，13704-45-5 94%
Reaction Conditions:
with triethylamine in isopropyl alcohol at 20; for 0.25 h;Eschenmoser Methylenation;
Steps:
synthesis of 3-methylenedihydrofuran-2(3H)-one (3c)
To a solution of a-dimethylaminomethyl-g-butyrolactone 1c (143 mg, 1.01 mmol) in 2-PrOH (5.0 mL) were added CDMT (176 mg, 1.01 mmol, 1.0 eq.) and Et3N (141 μL, 1.01 mmol, 1.0 eq.) at room temperature. After being stirred for 15 minutes, the reaction mixture was partitioned between Et2O and brine. The aqueous phase was extracted with Et2O three times and the combined organic phases were dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (hexane: dichloromethane: acetone = 10:1:1) to afford 3c (77.2 mg, 77 %), admixed with 4 (176.3 mg, 94 %). 1H NMR (CDCl3) d 6.27(m, 1H), 5.68(m, 1H), 4.38 (m, 2H), 2.99(m, 2H); 13C NMR (CDCl3) d 170.7, 133.4, 122.2, 65.2, 27.2; IR (CHCl3) cm-1: 2997, 2918, 1776, 1747, 1666, 1439, 1400, 1371, 1286, 1277, 1119, 1111, 1024, 945; LRMS (EI): 98 ([M]+ ).
References:
Yamada, Kohei;Masaki, Kazumasa;Hagimoto, Yuri;Kamiya, Seina;Kunishima, Munetaka [Tetrahedron Letters,2013,vol. 54,# 13,p. 1758 - 1760] Location in patent:supporting information
61541-20-6
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