Acetic Acid → HCID 17606704、化合物

反応式

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH2:11].CO[C:15]([CH3:17])=[CH2:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][CH:15]([CH3:17])[CH3:16]

参加物

反応物 5

HCID 176Acetic Acid

HCID 83002-Methoxypropene

HCID 14798Sodium Hydroxide

HCID 78878Methyl 2-amino-5-chlorobenzoate

HCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 17606704HCID 17606704、化合物収率 80%

実験手順

To a solution of 500 mg of 2-amino-5-chlorobenzoic acid methyl ester (2.69 mmol) were added slowly 380 μl of 2-methoxypropene (4.04 mmol), 154 μl of acetic acid (2.69 mmol) and 951 mg of sodium triacetoxyborohydride (4.04 mmol). The reaction mixture was stirred at RT for 3.5 d, then 1N NaOH solution was added and the mixture was extracted with DCM. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The remaining residue was purified by column chromatography (silica gel; heptane 100% to heptane/EtOAc 9:1) to give 488 mg (80%) of a yellow liquid. MS (ISP) 228.1 (M+H)+.