Water → HCID 59217793、化合物

HRID 2246490

反応式

HRID 2246490 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1.[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH:29]=[O:30].O>CCCCCC.O1CCCC1>[Br:25][C:26]1[CH:27]=[C:28]([CH:29]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[OH:30])[CH:31]=[CH:32][C:33]=1[O:34][CH3:35]

参加物

7

反応物 4

HCID 962WaterHCID 986623-Bromo-4-methoxybenzaldehydeHCID 57809595((4-Bromophenyl)ethynyl)triisopropylsilaneHCID 178418339Butyllithium

生成物 1

HCID 59217793HCID 59217793、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

14.8 mL of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 8.0 g 1-bromo-4-triisopropylsilylethynyl-benzene in 80 mL dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 5.1 g 3-bromo-4-methoxy-benzaldehyde dissolved in 20 mL tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm to ambient temperature overnight. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1).

後処理

  1. additionare added dropwise over 15 min
  2. waitThe resulting solution is left in the cooling bath
  3. temperatureto warm to ambient temperature overnight
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customthe solvent is removed
  7. customThe residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1)

出典と根拠

ORDレコード
ord-c585e4de99e748a285166be8d639f9b9
出典データセット
uspto-grants-2010_03
特許番号
US07687469B2

関連ノート

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