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Water → Methyl 3-(3-oxo-6-pentyloxyindan-5-yloxymethyl)benzoate

HRID 242448
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HRID 242448 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C:7](=[O:12])[CH2:6][CH2:5]2.I[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:19](=O)([O-])[O-].[Cs+].[Cs+].O.CC[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[C:33]([O:36][CH2:37]C)(=[O:35])[CH3:34]>CN(C=O)C>[O:12]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:32][CH2:31][CH2:30][CH2:29][CH3:28])=[C:10]([O:11][CH2:18][C:17]3[CH:19]=[C:34]([CH:14]=[CH:15][CH:16]=3)[C:33]([O:36][CH3:37])=[O:35])[CH:9]=2)[CH2:5][CH2:6]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 962WaterHCID 10796Cesium carbonateHCID 123351-IodopentaneHCID 115934875,6-Dihydroxy-2,3-dihydro-1H-inden-1-oneHCID 21899848Ethylacetate heptane

생성물 1

HCID 57458787Methyl 3-(3-oxo-6-pentyloxyindan-5-yloxymethyl)benzoate수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
40 °C

실험 절차

A mixture of 5,6-dihydroxyindanone (2.2 g; 13.4 mmol), iodopentane (1.75 ml; 13.4 mmol) and caesium carbonate (Cs2CO3; 4.8 g; 14.7 mmol) in DMF (50 ml) is heated at 40° C. for 35 minutes. The medium is cooled to room temperature, poured into water and extracted with methylene chloride. The combined organic phases are washed with water, dried over sodium sulfate and then concentrated (1.9 g solid). Flash chromatography (85/15 heptane/ethyl acetate) gives the expected product (1.5 g; 48% yield).

후처리

  1. temperatureThe medium is cooled to room temperature
  2. extractionextracted with methylene chloride
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated (1.9 g solid)

출처 및 근거

ORD 기록
ord-90ea986a78e840c3a15e3213c4923d6b
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08653134B2

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