Water → HCID 22147964, compound

HRID 1823895Notes

Reaction equation

HRID 1823895 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][C:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[CH:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[CH:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 597122936-heptynoic acid N-benzylamide

Product 1

HCID 22147964HCID 22147964, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1 m in THF, 10 ml, 10 mmol) was added to a solution of the amide from Step 1 (1.0 g, 4.6 mmol) in THF (20 ml) and the mixture was heated at reflux for 16 hours. The reaction was cooled in ice and treated successively with water (0.4 ml), sodium hydroxide (0.4 ml) and water (1.2 ml) allowing 10 minutes between additions. The mixture was filtered through a bed of Celite® and washed through with THF. The filtrate was evaporated in vacuo to provide 7-(N-benzylamino)hept-1-yne as a yellow oil (924 mg, 99%). (ES+) 202 ([MH]+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe reaction was cooled in ice
  4. filtrationThe mixture was filtered through a bed of Celite®
  5. washwashed through with THF
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-867fe33287e04b0092baa5d445351b7a
Source dataset
uspto-grants-2006_05
Patent number
US07041688B2

Reaction notes

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