Lithium → HCID 22602338, compound

HRID 2308403Notes

Reaction equation

HRID 2308403 reaction equation
[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]

Participants

4

Reactant 3

HCID 3028194LithiumHCID 22602329HCID 22602329, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22602338HCID 22602338, compound

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-77830d3c34034625b528fc918b357acc
Source dataset
uspto-grants-2004_12
Patent number
US06835846B2

Reaction notes

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