ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

tert-Butyl acrylate → 4-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic Acid Methyl Ester

HRID 220820
ノート
印刷プレビュー

反応式

HRID 220820 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[CH:14]=[CH2:15].C([O-])(=O)C.[Na+]>CC(N(C)C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2](/[CH:15]=[CH:14]/[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:3]([CH3:12])[CH:4]=1
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

6

反応物 3

HCID 15458tert-Butyl acrylateHCID 517045Sodium AcetateHCID 3294148Methyl 4-bromo-3-methylbenzoate

生成物 1

HCID 575553844-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic Acid Methyl Ester収率 40.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
140 °C

実験手順

Tetrakis(triphenylphosphine)palladium (0) (5.0 g, 4.33 mmol) was added to a stirred solution of methyl 4-bromo-3-methylbenzoate (9.93 g, 43.3 mmol), tert-butyl acrylate (50 ml, 341.3 mmol) and sodium acetate (35.8 g, 436.4 mmol) in DMA (350 ml). The mixture was heated at 140° C. for 5 h, filtered through Celite® filter agent and the filtrate was concentrated in vacuo. The residue was redissolved in EtOAc, washed with 0.3M KHSO4 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane to 20% EtOAc:80% hexane) to yield the title compound (4.81 g, 40%).

後処理

  1. filtrationfiltered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was redissolved in EtOAc
  5. washwashed with 0.3M KHSO4
  6. dry with materialbrine, dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane to 20% EtOAc:80% hexane)

出典と根拠

ORDレコード
ord-1f0a08724f0c49a089dcf31bcc33b40b
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202858B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート