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Benzaldehyde → Methyl[3,5-dichloro-4-(4-benzylaminophenoxy)phenyl]acetate

HRID 857158
ノート
印刷プレビュー

反応式

HRID 857158 の反応式
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[C:7]([Cl:20])[CH:6]=1.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)=[C:7]([Cl:20])[CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21867227HCID 21867227、化合物

生成物 1

HCID 21867255Methyl[3,5-dichloro-4-(4-benzylaminophenoxy)phenyl]acetate収率 88.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 887Methanol
溶媒

実験手順

A stirred mixture consisting of methyl[3,5-dichloro-4-(4-aminophenoxy)phenyl]acetate (0.32 g), benzaldehyde (0.20 g), sodium cyanoborohydride (0.03 g), methanol (15 mL) and one drop of acetic acid was stirred at room temperature for 5 days. The reaction mixture was concentrated and the residue partionated between ethyl acetate and sodium hydrogen-carbonate (saturated aqueous solution). The aqueous phase was further extracted with ethyl acetate. The collected organic phases were purified on column (silica gel, n-heptane/ethyl acetate, 9:1) to give 0.36 g of methyl[3,5-dichloro-4-(4-benzylaminophenoxy)phenyl]acetate.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe aqueous phase was further extracted with ethyl acetate
  3. customThe collected organic phases were purified on column (silica gel, n-heptane/ethyl acetate, 9:1)

出典と根拠

ORDレコード
ord-20959f241126469db4f1c93a84be82a3
出典データセット
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07144909B2

反応ノート

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