ChemicalBook CAS DataBase List CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID METHYL ESTER

CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID METHYL ESTER synthesis

12synthesis methods

Product Name:CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID METHYL ESTER
CAS Number:2734-47-6
Molecular formula:C21H32O2
Molecular Weight:316.48

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

10417-94-4 Synthesis

10417-94-4
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$19.00/10mg

CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID METHYL ESTER

2734-47-6
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$25.00/10mg

Yield: 98%

Reaction Conditions:

Stage #1:all cis-5,8,11,14,17-eicosapentaenoic acid with oxalyl dichloride in benzene at 20; for 2 h;
Stage #2:methanol at 0 - 20; for 2 h;

Steps:

1 Synthesis of methyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate (2):
To a stirred solution of (5Z,8Z,l lZ,14Z,17Z)-icosa-5,8,l l,14,17-pentaenoic acid 1 (30 g, 0.099 mol) in benzene (130 ml) at room temperature, oxalyl chloride (25.1 g, 0.198 mol) was added drop wise and allowed to stir at rt for 2h. After removal of benzene under vacuum, the residue was cooled to 0°C and MeOH was added slowly. The mixture was stirred at rt for 2h and concentrated under reduced pressure to obtain 2 (31 g, 98%) as a yellow liquid. ¹H NMR (400 MHz, CDC1₃): δ 5.32 (m, 10H), 3.667 (s, 3H), 2.82 (m, 8H), 2.32 (m, 2H), 2.07 (m, 2H), 1.71 (m, 2H), 0.87 (m, 3H).

References:

RAO M, Surya WO2017/68477, 2017, A1 Location in patent:Page/Page column 56-57