Acetic Acid → Ethyl 2-[3-[N-(4-Chlorobenzyl)aminomethyl]phenoxy]-2-methylpropionate

HRID 480684ノート

反応式

HRID 480684 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=O.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)(Cl)Cl>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][CH2:1][C:3]2[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=2)[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 660364-ChlorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18766496Ethyl 2-(3-formylphenoxy)-2-methylpropanoate

生成物 1

HCID 18766446Ethyl 2-[3-[N-(4-Chlorobenzyl)aminomethyl]phenoxy]-2-methylpropionate

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6212Chloroform溶媒

実験手順

Ethyl 2-(3-formylphenoxy)-2-methylpropionate (25 g, 105.8 mmol) was dissolved in 1,2-dichloroethane (300 mL). Subsequently, 4-chlorobenzylamine (15.44 mL, 127.0 mmol) and acetic acid (7.26 mL, 127.0 mmol) were added thereto, and the resultant mixture was stirred for 20 minutes at 0° C. Subsequently, sodium (triacetoxy)borohydride [NaBH(OAc)3 (26.91 g, 127.0 mmol)] was added thereto, and the mixture was stirred for five hours at room temperature. After completion of reaction, chloroform was added. Washing was performed sequentially with aqueous saturated sodium bicarbonate, water, and saturated brine, followed by drying over magnesium sulfate. The reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby a yellow oil was obtained (35.27 g, 92%).

後処理

  1. additionwas added
  2. washWashing
  3. dry with materialby drying over magnesium sulfate
  4. filtrationThe reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby a yellow oil
  5. customwas obtained (35.27 g, 92%)

出典と根拠

ORDレコード
ord-391fd4c2304d4c708005fedc0f65078d
出典データセット
uspto-grants-2003_11
特許番号
US06653334B1

反応ノート

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