Lithium → HCID 22602338、化合物

HRID 2308403ノート

反応式

HRID 2308403 の反応式
[Li].CC(C)([O-])C.[K+].[CH3:8][CH:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:10][CH2:11][C:12]#[C:13][CH3:14]>>[CH3:8][CH:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:10][CH2:11][CH2:12][C:13]#[CH:14]

参加物

4

反応物 3

HCID 3028194LithiumHCID 22602329HCID 22602329、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 22602338HCID 22602338、化合物

反応条件

温度
70 °C

実験手順

To anhydrous 1,3-diaminopropane (180 ml), which had been distilled, metallic lithium (2.8 g, 0.4 mol) was added under argon stream, and the mixture was stirred for 2 hours at 70° C. After the mixture was allowed to cool, potassium t-butoxide (27 g, 0.24 mol) was added, followed by stirring for 15 minutes. The 6-methyl-2-pentadecyne (6″) (12.1 g, 54.5 mmols) was added dropwise, and the mixture was stirred overnight at room temperature. This reaction was carefully quenched with a saturated aqueous solution of ammonium chloride, and then the mixture was extracted with ether. The resulting organic layer was washed (diluted hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride), dried (magnesium sulfate), and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6-methyl-1-pentadecyne (7″) (9.90 g, 82%). IR and 1H-NMR analysis of the product showed the following results: IR (film) 3300 (m,C≡CH), 2130 cm−1 (w,C≡C). 1H-NMR (90 MHz, CDCl3) 0.84 (3H,d,J=7,6-Me), 0.88 (3H,t,J=7,15-H), 1.0-1.6 (21H,m,4˜14-H), 1.93 (1H,t,J=2.5,1-H), 2.0-2.3 (2H,m,3-H).

後処理

  1. distillationTo anhydrous 1,3-diaminopropane (180 ml), which had been distilled
  2. temperatureto cool
  3. stirringby stirring for 15 minutes
  4. stirringthe mixture was stirred overnight at room temperature
  5. customThis reaction was carefully quenched with a saturated aqueous solution of ammonium chloride
  6. extractionthe mixture was extracted with ether
  7. washThe resulting organic layer was washed (diluted hydrochloric acid
  8. dry with materiala saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride), dried (magnesium sulfate)
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-77830d3c34034625b528fc918b357acc
出典データセット
uspto-grants-2004_12
特許番号
US06835846B2

反応ノート

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