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Potassium Carbonate → 4-(4-Methoxy-2-nitrophenyl)indan-1-one

HRID 514759
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HRID 514759 반응식
C([O-])([O-])=O.[K+].[K+].CC1(C)C(C)(C)OB([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=[O:24])O1.Cl[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[N+:35]([O-:37])=[O:36].CCCCCC.C(OCC)(=O)C>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=[O:24])=[C:28]([N+:35]([O-:37])=[O:36])[CH:29]=1
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참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 251404-Chloro-3-nitroanisoleHCID 21226206Ethyl acetate hexaneHCID 220320882,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-one

생성물 1

HCID 673683614-(4-Methoxy-2-nitrophenyl)indan-1-one

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

Potash (7.5 g, 54.3 mmol) and Pd(PPh3)4(1.6 g, 1.4 mmol) were added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-1-one 34 (7.0 g, 27.1 mmol) and 4-chloro-3-nitroanisole (5.1 g, 27.1 mmol) in a mixture of dioxane (80 mL) and water (20 mL). The mixture obtained was heated to 80° C. under argon, kept at this temperature for 16 h (TLC monitoring, eluent: hexane-ethyl acetate, 1:1), cooled, filtered through Celite, evaporated, and dissolved in CH2Cl2. Then the mixture was filtered off from the insoluble portion, evaporated with silica gel, and purified on a short thick column with silica gel (eluent: hexane—CH2Cl2 100:0→0:100, CH2Cl2-ethyl acetate 100:0→50:50). Yield of 35: 5.59 g. The product was used in the next step without additional purification.

후처리

  1. customThe mixture obtained
  2. filtrationfiltered through Celite
  3. customevaporated
  4. dissolutiondissolved in CH2Cl2
  5. filtrationThen the mixture was filtered off from the insoluble portion
  6. customevaporated with silica gel
  7. custompurified on a short thick column with silica gel (eluent: hexane—CH2Cl2 100:0→0:100, CH2Cl2-ethyl acetate 100:0→50:50)
  8. customThe product was used in the next step without additional purification

출처 및 근거

ORD 기록
ord-287f9ac7a91f4a8397400d0b2b11dfcc
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108916B2

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