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Methyl 2-azidoacetate → 2-Azido-3-(4-bromo-5-methyl-thiophen-2-yl)-acrylic acid methyl ester

HRID 1951638
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인쇄 미리보기

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HRID 1951638 반응식
[CH3:1][O:2][C:3](=[O:8])[CH2:4][N:5]=[N+:6]=[N-:7].[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=O)[S:13][C:14]=1[CH3:15].C[O-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:8])[C:4]([N:5]=[N+:6]=[N-:7])=[CH:16][C:12]1[S:13][C:14]([CH3:15])=[C:10]([Br:9])[CH:11]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium MethoxideHCID 155382124-Bromo-5-methylthiophene-2-carbaldehyde

생성물 1

HCID 767450662-Azido-3-(4-bromo-5-methyl-thiophen-2-yl)-acrylic acid methyl ester수율 81.6%

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
0 °C

실험 절차

To a solution of azido-acetic acid methyl ester (25 g, 220 mmol) and 4-bromo-5-methyl-thiophene-2-carbaldehyde (15 g, 73 mmol) in 50 ml of MeOH cooled at −25° C. was added a solution NaOMe in MeOH (51 ml, 4.36 M). The resulting mixture (slush) was stirred with a mechanical stirrer for 2 h at 0° C. and the 200 g of ice was added. The yellow solid was collected by filtration and air-dried to give 18 g of the title product which was used for the next step without further purification.

후처리

  1. filtrationThe yellow solid was collected by filtration
  2. customair-dried

출처 및 근거

ORD 기록
ord-911601a7ec7648e4bfee224b19ff85a6
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08404736B2

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