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

HRID 480684노트

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HRID 480684 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6212Chloroform용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-391fd4c2304d4c708005fedc0f65078d
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06653334B1

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