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Ethyl Acrylate → Ethyl (E)-3-(2-chloropyrimidin-5-yl)acrylate

HRID 226392
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HRID 226392 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH:32]=[CH2:33].C(N(CC)C(C)C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5](/[CH:33]=[CH:32]/[C:31]([O:35][CH2:36][CH3:37])=[O:34])=[CH:4][N:3]=1
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참가 물질

7

반응물 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 17142232-Chloro-5-iodopyrimidine

생성물 1

HCID 53259409Ethyl (E)-3-(2-chloropyrimidin-5-yl)acrylate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

To a mixture of 2-chloro-5-iodopyrimidine (7.62 g), palladium(II) acetate (356 mg), tri(o-tolyl)phosphine (965 mg), and DMF (32 mL) was added ethyl acrylate (17.2 mL) and N,N-diisopropylethylamine (13.8 mL). After stirring for 3 hours at 100° C., the reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(2-chloro-5-pyrimidinyl)acrylate (2.32 g).

후처리

  1. customthe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-b212646e797944888b766c08bba54603
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557127B2

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