Ethylene Glycol → HCID 178517865、化合物

HRID 215960ノート

反応式

HRID 215960 の反応式
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22](I)[CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)CCC.[Cu]I.O>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[C:24]([N:15]2[CH2:16][CH2:17][C:10]3([C:9](=[O:18])[N:8]([C@H:5]4[CH2:4][CH2:3][C@@H:2]([OH:1])[CH2:7][CH2:6]4)[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)[CH:25]=1

参加物

8

反応物 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 178517868HCID 178517868、化合物

生成物 1

HCID 178517865HCID 178517865、化合物収率 70%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 2631-Butanol溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-(cis-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one (0.50 g, 2.0 mmol), 4-bromo-1-fluoro-2-iodobenzene (0.894 g, 2.97 mmol), copper(I) iodide (0.0586 g, 0.308 mmol), potassium phosphate (1.26 g, 0.596 mmol) and 1,2-ethanediol (0.23 mL, 4.1 mmol) in 1-butanol (2.5 mL) was heated at 100° C. overnight. The reaction mixture was treated with water, extracted with ether. The combined organic layers were washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure. The residue was purified on a silica gel column with ethyl acetate in hexane (gradient: 0 to 50%) to give the desired product (0.59 g, 70%). LCMS: (M+H)+=425.0/427.0.

後処理

  1. extractionextracted with ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified on a silica gel column with ethyl acetate in hexane (gradient: 0 to 50%)

出典と根拠

ORDレコード
ord-d50c91e1934e43d382c73f612ede010c
出典データセット
uspto-grants-2012_06
特許番号
US08193207B2

反応ノート

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