Tetrahydrofuran → HCID 53721211, compound

HRID 329423Notes

Reaction equation

HRID 329423 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([N:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[CH3:10])=[CH:5][CH:4]=1)=[CH2:2].O1CCCC1.[Li].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C@H:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[CH3:10])=[CH:7][CH:8]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24436Sodium SulfateHCID 3028194LithiumHCID 86743636HCID 86743636, compound

Product 1

HCID 53721211HCID 53721211, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1 g of N-(6-methyl-pyridine-2-carbaldehyde)-(R)-1-(4-vinylphenyl)-ethylimine (Example 1) and 5 ml of dry tetrahydrofuran is added dropwise to a mixture of 5 ml of dry tetrahydrofuran and 0.42 g of lithium alanate at 0° C. and in the absence of moisture. The mixture is then stirred for 4 hours without cooling, after which it is hydrolysed at 0° C. with 1 ml of concentrated sodium sulfate solution. The precipitate is filtered off and washed with ethyl acetate. The aqueous phase of the filtrate is separated off and rinsed with ethyl acetate, and the combined organic phases are dried over sodium sulfate. After the solvent has been evaporated off at room temperature and under about 1.5 Pa, the residue is distilled in a bulb tube furnace at a furnace temperature of 250° C. and under 0.01 Pa. 0.63 g (63% of theory) of a yellow oil is obtained. [α]D20 =+52.9 (0.926, chloroform). 250 MHz-1HFT-NMR (CDCl3): δ=1.41 (d; 3H), 2.26 (broad; 1H), 2.53 (s; 3H), 3.70 (s; 2H), 3.82 (q; 1H), 5.21 (m; 1H), 5.72 (m; 1H), 6.71 (m; 1H), 6.97-7.50 (m; 7H)ppm.

Workup

  1. temperaturewithout cooling
  2. filtrationThe precipitate is filtered off
  3. washwashed with ethyl acetate
  4. customThe aqueous phase of the filtrate is separated off
  5. washrinsed with ethyl acetate
  6. dry with materialthe combined organic phases are dried over sodium sulfate
  7. customAfter the solvent has been evaporated off at room temperature and under about 1.5 Pa
  8. distillationthe residue is distilled in a bulb tube furnace at a furnace temperature of 250° C.
  9. custom0.63 g (63% of theory) of a yellow oil is obtained

Sources & evidence

ORD record
ord-001df9a3a8a544cc9f86663c85b63d07
Source dataset
uspto-grants-1990_01
Patent number
US04891412

Reaction notes

Loading…