Water → HCID 69059481、化合物

HRID 2103614ノート

反応式

HRID 2103614 の反応式
Br[C:2]1[S:3][CH:4]=[C:5]([S:7]([CH3:10])(=[O:9])=[O:8])[CH:6]=1.[F-].[Cs+].[CH:13]1([CH:18]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14]1.O>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:13]1(/[CH:18]=[C:19](\[C:2]2[S:3][CH:4]=[C:5]([S:7]([CH3:10])(=[O:9])=[O:8])[CH:6]=2)/[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

7

反応物 4

HCID 962WaterHCID 25953Cesium fluorideHCID 670847173-Cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-olHCID 674844052-Bromo-4-(methylsulfonyl)thiophene

生成物 1

HCID 69059481HCID 69059481、化合物

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

Add 2-bromo-4-methanesulfonyl-thiophene (241 mg, 1.0 mmol), caesium fluoride ( 304 mg, 2.0 mmol) and tetrakis-(triphenylphosphin)-palladium(0) (58 mg, 0.05 mmol) to a solution of 3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (252 mg, 1.0 mmol) in THF. Stir at 50° C. for 24 h, monitore completion of the reaction by LCMS. Treat the reaction mixture with water and extract with ethyl acetate. Dry organic layers over sodium sulfate and remove solvents under vacuum to obtain 405 mg crude product. Purify by silica gel chromatography, eluting with gradient from 9:1 to 1:1 hexane:ethyl acetate to obtain 118 mg purified product. MS (m/e): 309.0 (M+Na).

後処理

  1. custommonitore completion of the reaction by LCMS
  2. extractionextract with ethyl acetate
  3. customDry organic layers over sodium sulfate and remove solvents under vacuum
  4. customto obtain 405 mg crude product
  5. customPurify by silica gel chromatography
  6. washeluting with gradient from 9:1 to 1:1 hexane
  7. customethyl acetate to obtain 118 mg
  8. custompurified product

出典と根拠

ORDレコード
ord-c51b99adf5324355a8e16c09c68d36f5
出典データセット
uspto-grants-2009_08
特許番号
US07576108B2

反応ノート

読み込み中…