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Potassium Carbonate → 5-[4-Ethoxy-2-(3-hydroxymethyl-oxetan-3-ylmethoxy)-3-methoxy-phenyl]-3H-isobenzofuran-1-one

HRID 2171138
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HRID 2171138 반응식
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([OH:20])[C:5]=1[O:21][CH3:22])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]1([CH2:35][OH:36])[CH2:34][O:33][CH2:32]1>C(#N)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([O:20][CH2:30][C:31]2([CH2:35][OH:36])[CH2:34][O:33][CH2:32]2)[C:5]=1[O:21][CH3:22])[CH3:2]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 529264[3-(Bromomethyl)oxetan-3-yl]methanolHCID 701700835-(4-Ethoxy-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one

생성물 1

HCID 674678445-[4-Ethoxy-2-(3-hydroxymethyl-oxetan-3-ylmethoxy)-3-methoxy-phenyl]-3H-isobenzofuran-1-one수율 28.2%

시약·촉매·용매 1

HCID 6342Acetonitrile
용매

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온도
80 °C

실험 절차

To a stirring solution of 5-(4-ethoxy-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one (80 mg, 0.266 mmol) in acetonitrile (7 mL) was added potassium carbonate (110 mg, 0.798 mmol) and (3-Bromomethyl-oxetan-3-yl)-methanol (96 mg, 0.532 mmol) and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 0-25% ethyl acetate in pet ether) afforded title compound as a solid (30 mg, 28%).

후처리

  1. customthe resultant reaction mixture
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification of the residue by flash column chromatography (silica gel, 0-25% ethyl acetate in pet ether)

출처 및 근거

ORD 기록
ord-00fa7bdf52c34b0d9aa7d558f9661d1d
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051290B2

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