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Diisopropylamine → 2-Fluoro-3-octyl-6-(4-octyloxyphenyl)pyridine

HRID 1780547
ノート
印刷プレビュー

反応式

HRID 1780547 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:21]=2)[N:15]=1.Br[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>O1CCCC1.CCCCCC.O>[F:13][C:14]1[C:19]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:21]=2)[N:15]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 81401-BromooctaneHCID 179115002-(4-Octyloxyphenyl)-6-fluoropyridineHCID 178418339Butyllithium

生成物 1

HCID 190469322-Fluoro-3-octyl-6-(4-octyloxyphenyl)pyridine収率 3.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒3 回
HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

0.74 g (7.3 mmol) of diisopropylamine in 30 ml of tetrahydrofuran is stirred at 0° C. with 4.56 ml (7.3 mmol) of a 1.6-molar n-butyllithium solution in hexane under argon for 1 hour. After cooling to -78° C., 2.00 g (6.64 mmol) of 2-fluoro-6-(4-octyloxyphenyl)pyridine in 30 ml of tetrahydrofuran are added dropwise at such a rate that the temperature does not exceed 70° C. After 4 hours at -78° C., 1.35 g (7.00 mmol) of 1-bromooctane in 10 ml of tetrahydrofuran are added dropwise while also maintaining a temperature ≤-70° C. The reaction mixture is stirred overnight, during which it warms to room temperature, 5 ml of water are added, and the mixture is evaporated to dryness. The residue is taken up in ether, the resulting solution is washed twice with water, the organic phase is dried over sodium sulfate, filtered, the solvent is distilled off, the residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate) and recrystallized from acetonitrile, giving 0.10 g of 2-fluoro-3-octyl-6-(4-octyloxyphenyl)pyridine, whose physical properties are identical to those of the product prepared by Example 1.

後処理

  1. customdoes not exceed 70° C
  2. temperaturealso maintaining a temperature ≤-70° C
  3. customwarms to room temperature
  4. customthe mixture is evaporated to dryness
  5. washthe resulting solution is washed twice with water
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. distillationthe solvent is distilled off
  9. customthe residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate)
  10. customrecrystallized from acetonitrile

出典と根拠

ORDレコード
ord-28d28a7ea4c741239408e610d360cdb4
出典データセット
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05630962

反応ノート

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