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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
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인쇄 미리보기

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HRID 19398 반응식
[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]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 66899808HCID 66899808, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 8028
Tetrahydrofuran
용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-001925c05344414d945b079d98bac1e9
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741327B2

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