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Phthalimide → 2-(5-(2-Cyclopropylvinyl)thiophen-2-ylmethyl)isoindol-1,3-dione

HRID 2080140
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HRID 2080140 반응식
[CH:1]1([CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11]O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12.COC(N=NC(OC)=O)=O>O1CCCC1.O>[CH:1]1([CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11][N:36]3[C:32](=[O:42])[C:33]4[C:34](=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:35]3=[O:37])=[CH:8][CH:7]=2)[CH2:2][CH2:3]1
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참가 물질

7

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 67119677(5-(2-Cyclopropylvinyl)thiophen-2-yl)methanol

생성물 1

HCID 671195832-(5-(2-Cyclopropylvinyl)thiophen-2-ylmethyl)isoindol-1,3-dione수율 20.6%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

(5-(2-Cyclopropylvinyl)thiophen-2-yl)methanol described in Preparation Example 149 (930 mg, 5.19 mmol), triphenylphosphine (2040 mg, 7.78 mmol) and phthalimide (1140 mg, 7.78 mmol) were dissolved in tetrahydrofuran (50 mL), azodicarboxylic acid dimethyl ester (1140 mg, 7.78 mmol) was added under stirring at room temperature, and the solution was stirred for 1 hour. Water (50 mL) was added to the reaction solution, which was then extracted with ethyl acetate (50 mL). The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=9:1), and the title compound (330 mg, 1.07 mmol, 20.6%) was obtained as a white solid.

후처리

  1. stirringthe solution was stirred for 1 hour
  2. extractionwas then extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=9:1)

출처 및 근거

ORD 기록
ord-2d298c00649e4899b21c8af722e2b048
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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