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Acetonitrile → methyl 5,6-dimethoxy-1H-indene-2-carboxylate

HRID 2175693
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HRID 2175693 반응식
I[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=O.CCN(CCOC1C=CC(CC2C=CC=CC=2)=CC=1)CC.Cl.C(#N)C.[C:39]([O:43][CH3:44])(=[O:42])[CH:40]=[CH2:41]>[Zn].O>[CH3:13][O:12][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][C:8]=1[O:10][CH3:11])[CH2:41][C:40]([C:39]([O:43][CH3:44])=[O:42])=[CH:4]2
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참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 7294Methyl AcrylateHCID 175534Tesmilifene HydrochlorideHCID 110117632-Iodo-4,5-dimethoxybenzaldehyde

생성물 1

HCID 12423472methyl 5,6-dimethoxy-1H-indene-2-carboxylate수율 21.3%

시약·촉매·용매 2

HCID 23994Zinc
촉매
HCID 962Water용매

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온도
80 °C

실험 절차

2-Iodo-4,5-dimethoxybenzaldehyde (292 mg, 1.0 mmol), CoCl2 (dppe) complex (26.4 mg, 0.05 mmol), dppe (19.9 mg, 0.05 mmol) and zinc power (179.8 mg, 2.75 mmol) were placed in a vial, which was sealed with a septum and flushed several times with nitrogen. Acetonitrile (3 mL) and methyl acrylate (172 mg, 2.0 mmol) were then sequentially added and the mixture was heated at 80° C. overnight. Water was then added and the mixture was extracted with ethyl acetate. The organic extracts were concentrated under reduced pressure and the residue was purified by flash chromatography using petroleum ether/ethyl acetate 8:1 (v:v) as eluent to give methyl 5,6-dimethoxy-1H-indene-2-carboxylate (50 mg, 21%). LC-MS (ES-API); rt 7.89 min; m/z calculated for C13H14O4 [M+H]+ 235.1, found 235.1.

후처리

  1. customwas sealed with a septum
  2. customflushed several times with nitrogen
  3. extractionthe mixture was extracted with ethyl acetate
  4. concentrationThe organic extracts were concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-14bd130193fc4188902ee66da0fcd1c8
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062076B2

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