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Tributylphosphine → {4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetic Acid Ethyl Ester

HRID 984943
ノート
印刷プレビュー

反応式

HRID 984943 の反応式
C(P(CCCC)CCCC)CCC.[CH2:14]([O:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([Cl:26])[CH:20]=1)[CH3:15].[Br:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([C:39]2[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=2)=[CH:36][CH2:37]O)=[CH:31][CH:30]=1>C1COCC1>[CH2:14]([O:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:37][CH:36]=[C:35]([C:32]2[CH:31]=[CH:30][C:29]([Br:28])=[CH:34][CH:33]=2)[C:39]2[CH:40]=[CH:41][C:42]([Br:45])=[CH:43][CH:44]=2)=[C:21]([Cl:26])[CH:20]=1)[CH3:15]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 13831TributylphosphineHCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetateHCID 222703043,3-Bis-(4-bromophenyl)prop-2-en-1-ol

生成物 1

HCID 10120503{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetic Acid Ethyl Ester収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
2.5 °C

実験手順

A solution of tributylphosphine (955 μl, 3.0 mmol), 3-chloro-4-hydroxyphenylacetic acid ethyl ester (472 mg, 2.2 mmol) and 3,3-bis-(4-bromophenyl)prop-2-en-1-ol (736 mg, 2.0 mmol) in dry THF (15 ml) was stirred at 0-5° C. for 30 min, under a atmosphere of nitrogen. Azodicarboxylic dipiperidide (756 mg, 3.0 mmol) was added the mixture stirred at 0-5° C. for 2 h, and at room temperature over night. The reaction mixture was filtered and the filtrate concentrated in vacuo. The crude product was then purified by column chromatography on silica (eluent graduated from heptane to toluene) to give 1.0 g (89%) of the title compound.

後処理

  1. waitat room temperature over night
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude product was then purified by column chromatography on silica (eluent graduated from heptane to toluene)

出典と根拠

ORDレコード
ord-747732c38f2f4f44ace3fc8d8176d064
出典データセット
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06869967B2

反応ノート

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