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

HRID 514759
ノート
印刷プレビュー

反応式

HRID 514759 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-287f9ac7a91f4a8397400d0b2b11dfcc
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108916B2

反応ノート

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