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Potassium Carbonate → (E)-3-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-but-2-enoic acid ethyl ester

HRID 19398
ノート
印刷プレビュー

反応式

HRID 19398 の反応式
[CH3:1][C:2]1([CH3:15])[O:6][C@@H:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([O:24][C:25](=[O:29])[C:26]#[C:27][CH3:28])[CH3:23]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:22]([O:24][C:25](=[O:29])/[CH:26]=[C:27](/[O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C@H:5]2[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:6]2)=[CH:9][CH:10]=1)\[CH3:28])[CH3:23]
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 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 66899808HCID 66899808、化合物

生成物 1

HCID 66895027(E)-3-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-but-2-enoic acid ethyl ester収率 41%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol (0.696 g, 3.34 mol), potassium carbonate (0.463 g, 0.003 mol), ethyl-2-butynoate (2.25 g, 0.020 mol) and a catalytic amount of 4-dimethylaminopyridine in tetrahydrofuran (15 mL) was placed in a sealed tube and heated at 80° C. for 6 h. The reaction mixture was cooled, filtered and the isolated solids washed with tetrahydrofuran. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) which afforded (E)-3-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-but-2-enoic acid ethyl ester (0.440 g, 41%) as a colorless oil.

後処理

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washthe isolated solids washed with tetrahydrofuran
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) which

出典と根拠

ORDレコード
ord-001925c05344414d945b079d98bac1e9
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741327B2

反応ノート

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