Hydrochloric Acid → 1-[3-(cyclopentyloxy)-2-hydroxy-4-methoxyphenyl]Ethanone

HRID 20625

반응식

HRID 20625 반응식
[OH:1][C:2]1[C:7]([OH:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].Br[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[CH:15]1([O:8][C:7]2[C:2]([OH:1])=[C:3]([C:11](=[O:13])[CH3:12])[CH:4]=[CH:5][C:6]=2[O:9][CH3:10])[CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 128202,3-Dihydroxy-4-Methoxyacetophenone

생성물 1

HCID 687411251-[3-(cyclopentyloxy)-2-hydroxy-4-methoxyphenyl]Ethanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

A mixture of 1-(2,3-dihydroxy-4-methoxyphenyl)ethanone (10 g, 55 mmol), bromocyclopentane (6.0 mL, 56 mmol), potassium carbonate (15.5 g, 112 mmol), and anhydrous DMF (100 mL) was heated at 110° C. under N2 for 17 h and then allowed to cool to rt. The mixture was poured into 0.5N HCl (600 mL) and extracted with diethyl ether (250 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (1:0→17:3; hexanes:ethyl acetate) to give 1-[3-(cyclopentyloxy)-2-hydroxy-4-methoxyphenyl]ethanone: MS (ESI): 251.2.

후처리

  1. temperatureto cool to rt
  2. extractionextracted with diethyl ether (250 mL×2)
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (1:0→17:3; hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-d4277139295b4d52a08421ba5a29dc35
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745646B2

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