Sodium hydride → HCID 59557729、化合物

HRID 1175323ノート

反応式

HRID 1175323 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][OH:22].[H-].[Na+].Br[CH2:26][C:27]#[C:28][CH3:29]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][O:22][CH2:26][C:27]#[C:28][CH3:29]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 595577063-(2-Bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol

生成物 1

HCID 59557729HCID 59557729、化合物収率 65.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 3-(2-bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol (BL) (0.268 g, 0.70 mmol) in 5 mL of THF was added NaH (0.034 g, 0.84 mmol, 60%) and stirred for 40 min. 1-bromo-2-butyne (0.094 mL, 1.05 mmol) was added and the mixture was stirred overnight at room temperature. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, concentrated and purified by preparative TLC (eluting with EtOAc:PE=1:10) to obtain 0.2 g of intermediate BM.

後処理

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by preparative TLC (eluting with EtOAc:PE=1:10)

出典と根拠

ORDレコード
ord-754414dff5ca4009b086c461394b7518
出典データセット
uspto-grants-2010_11
特許番号
US07838498B2

反応ノート

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