Hydrochloric Acid → 1-Chloro-8-diethylamino-5-hydroxy-5-methyl-6-octyne

HRID 1738788Notes

Reaction equation

HRID 1738788 reaction equation
C([Li])CCC.[CH2:6]([N:8]([CH2:11][C:12]#[CH:13])[CH2:9][CH3:10])[CH3:7].[Cl:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20].Cl>CCCCCC.O1CCCC1>[Cl:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])([CH3:20])[C:13]#[C:12][CH2:11][N:8]([CH2:9][CH3:10])[CH2:6][CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 20010DietylaminopropinHCID 824686-Chlorohexan-2-oneHCID 178418339Butyllithium

Product 1

HCID 153832251-Chloro-8-diethylamino-5-hydroxy-5-methyl-6-octyne

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

12.37 ml (19.8 mmol) of a 1.6 M solution of n-butyllithium in n-hexane were slowly added dropwise to a solution of 2.0 g (18 mmol) of N,N-diethyl-2-propynylamine (Example 1C1)) in 50 ml of tetrahydrofuran at -78° C. After one hour at -78° C., the mixture was warmed to room temperature, and 2.42 g (18 mmol) of 1-chloro-5-hexanone were added. Stirring at room temperature for one hour was followed by adjustment to pH 7 with 2 N hydrochloric acid and partitioning between 5% strength sodium bicarbonate solution and dichloromethane. The organic phase was dried over magnesium sulfate, the solvent was removed under reduced pressure. Yield: 4.38 (99% of theory); oily product

Workup

  1. customat -78° C
  2. custompartitioning between 5% strength sodium bicarbonate solution and dichloromethane
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dfe439db4b924c46bd1b0460cb55dfa2
Source dataset
uspto-grants-1999_10
Patent number
US05965555

Reaction notes

Loading…