ChemicalBook CAS DataBase List 1,3-Dioxolane-4-carboxylicacid,2,2-dimethyl-,methylester(9CI)

1,3-Dioxolane-4-carboxylicacid,2,2-dimethyl-,methylester(9CI) synthesis

8synthesis methods

Product Name:1,3-Dioxolane-4-carboxylicacid,2,2-dimethyl-,methylester(9CI)
CAS Number:108865-84-5
Molecular formula:C7H12O4
Molecular Weight:160.17

Potassium 2,2-dimethyl-1,3-dioxolane-4-carboxylate

83400-91-3
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$45.00/50mg

74-88-4
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$15.00/10g

1,3-Dioxolane-4-carboxylicacid,2,2-dimethyl-,methylester(9CI)

108865-84-5
23 suppliers
$361.00/10g

Yield: 55%

Reaction Conditions:

with N,N,N,N,-tetramethylethylenediamine in acetonitrile at 60; for 6 h;

Steps:

3.2
A mixture of potassium 2,2-dimethyl-1,3-dioxolane-4-carboxylate (6.50 g, 35.28 mmol), iodomethane (5.50 mL, 88.35 mmol), N,N,N',N'-tetramethylethylenediamine (0.53 mL, 3.53 mmol) and acetonitrile (100 mL) was heated at about 60° C. for about 6 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The resulting residue was dissolved in ether and filtered. The filtrate was concentrated in vacuo to give the title product as a pale yellow liquid (3.10 g, 55%). ¹H NMR (400 MHz, CDCl₃) δ 1.41 (s, 3H), 1.51 (s, 3H), 3.78 (s, 3H), 4.07-4.13 (m, 1H), 4.21-4.26 (m, 1H), 4.56-4.62 (m, 1H); IR (film) υ 2992, 2950, 2890, 1757, 1446, 1377 cm^-1; MS 161 (M+1).

References:

AUSPEX PHARMACEUTICALS, INC. US2009/270469, 2009, A1 Location in patent:Page/Page column 30