Diethyl Ether → HCID 20266387, compound

HRID 1719719Notes

Reaction equation

HRID 1719719 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([CH2:14][CH2:15]C(OCC)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2].C[CH2:36][O:37]CC>>[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([CH:14]([CH3:15])[CH2:36][OH:37])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 70405840HCID 70405840, compound

Product 1

HCID 20266387HCID 20266387, compound

Procedure

1-benzyl-4-(1-ethoxycarbonyl)ethyl-1,2,3,6-tetrahydropyridine (18.0 g) in dry ether (70 cm3) was added dropwise at 0° to a stirred suspension of lithium aluminium hydride (2.7 g) in ether (70 cm3) over 0.5 hours. After 1 hour 1M sodium hydroxide (15 cm3) solution was added dropwise over 0.5 hours and after stirring for a further 1 hour magnesium sulphate (10 g) was added. The mixture was filtered, the filtrate evaporated in vacuo and the residue distilled to afford 1-benzyl-4-(1-hydroxyprop-2-yl)-1,2,3,6-tetrahydropyridine as an oil b.p. 200° 0.05 mm (Kugelrohr) (12.43 g).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated in vacuo
  4. distillationthe residue distilled

Sources & evidence

ORD record
ord-9c2965fcd53a4f3caa22edc87b183527
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

Loading…