Sodium Carbonate → 2-[2-(2-Fluoro-phenyl)cyclopent-2-enyl]-ethanol

HRID 9272

反応式

HRID 9272 の反応式
Br[C:2]1[CH:3]([CH2:7][CH2:8][OH:9])[CH2:4][CH2:5][CH:6]=1.C([O-])([O-])=O.[Na+].[Na+].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O>C1C=CC=CC=1.CCO.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>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:3]([CH2:7][CH2:8][OH:9])[CH2:4][CH2:5][CH:6]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 219860942-(2-Bromo-cyclopent-2-enyl)-ethanol

生成物 1

HCID 219861072-[2-(2-Fluoro-phenyl)cyclopent-2-enyl]-ethanol

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒2 回HCID 241Benzene溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

2-(2-Bromo-cyclopent-2-enyl)-ethanol Intermediate FIVE1 (1.21 g, 6.33 mmol) in benzene (40 mL), and Na2CO3 (7 mL, 2M) was treated with a solution of 2-fluorophenylboronic acid (1.08 g, 7.72 mmol) in EtOH (28 mL). Tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4 (0.38 g, 5 mol %) was added and the mixture was heated to 80° C. for 1.5 h. The mixture was diluted with water and extracted with diethyl ether (2×). The combined organic layers were dried over MgSO4, filtered and evaporated to dryness. The oil was purified by column chromatography on silica gel with 30% EtOAc:hexane to give 2-[2-(2-fluoro-phenyl)-cyclopent-2-enyl]-ethanol Intermediate FIVE2 (1.21 g).

後処理

  1. extractionextracted with diethyl ether (2×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe oil was purified by column chromatography on silica gel with 30% EtOAc

出典と根拠

ORDレコード
ord-5ee325071a0d46e99c30139f1c8099af
出典データセット
uspto-grants-2006_08
特許番号
US07091232B2

関連ノート

読み込み中…