ChemicalBook CAS DataBase List METHYL TRANS-2-HEXENOATE, 98

METHYL TRANS-2-HEXENOATE, 98 synthesis

14synthesis methods

Product Name:METHYL TRANS-2-HEXENOATE, 98
CAS Number:13894-63-8
Molecular formula:C7H12O2
Molecular Weight:128.17

67-56-1 Synthesis

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

13419-69-7 Synthesis

13419-69-7
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$10.00/1g

13894-63-8
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$22.00/25g

Yield: 100%

Reaction Conditions:

Stage #1:(E)-2-Hexenoic acid with oxalyl dichloride in tetrahydrofuran;N,N-dimethyl-formamide for 0.5 h;Cooling with ice;
Stage #2:methanol in tetrahydrofuran;N,N-dimethyl-formamide at 10 - 35; for 2 h;

Steps:

87 Methyl (2E)-hex-2-enoate
Reference Example 87
Methyl (2E)-hex-2-enoate
To a solution (100 mL) of (2E)-hex-2-enoic acid (5.0 g) in tetrahydrofuran were added dropwise under ice-cooling oxalyl chloride (3.76 mL) and N,N-dimethylformamide (1 mL).
The mixture was stirred at the same temperature for 30 min, methanol (10 mL) was gradually added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr.
The solvent was evaporated under reduced pressure, and the residue was treated with 6% aqueous sodium hydrogencarbonate solution, and extracted with diethyl ether.
The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure (50 Torr, water bath 10°C) to give the title compound as a colorless oil (yield 5.67 g, about 100%).
¹H-NMR (CDCl₃)δ:0.94 (3H, t, J=7.5 Hz), 1.43-1.53 (2H, m), 2.14-2.21 (2H, m), 3.73 (3H, s), 5.82 (1H, dt, J=1.8, 15.6 Hz), 6.97 (1H, dt, J=6.9, 15.6 Hz).

References:

Takeda Pharmaceutical Company Limited;Kajino, Masahiro;Hasuoka, Atsushi;Tarui, Naoki;Takagi, Terufumi EP2336107, 2015, B1 Location in patent:Paragraph 0261

13419-69-7 Synthesis

13419-69-7
248 suppliers
$10.00/1g