Aluminium lithium hydride → HCID 19870607, compound

HRID 330182Notes

Reaction equation

HRID 330182 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20](OC)=[O:21])=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=O)[CH2:8][CH3:9]>O1CCCC1>[OH:21][CH2:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([CH2:7][CH2:8][CH3:9])=[CH:12][NH:13]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22627259HCID 22627259, compound

Product 1

HCID 19870607HCID 19870607, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of lithium aluminum hydride (1.71 g) in dry tetrahydrofuran (90 ml) was added slowly via cannula to methyl 3-propionylindole-6-carboxylate (1.6 g) as a stirred suspension in dry tetrahydrofuran (60 ml) under an atmosphere of nitrogen. After addition was complete, the mixture was heated to reflux for 90 min, then cooled and poured carefully onto ice (200 ml). The mixture was extracted with ethyl acetate; the extracts were washed (water (twice), brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 7:3 hexane:ethyl acetate, to give 6-hydroxymethyl-3-propylindole (1.2 g, 92%) as a white solid; mp 68°-71°; partial NMR (250 MHz, DMSO-d6): 0.93(t, 3H, CH2CH3), 1.64(m, 2H, CH2CH3), 2.65(t, 2H, CH2CH2CH3), 4.55(d, 2H, CH2OH), 5.03(t, 1H, OH), 10.67(br s, 1H, NH).

Workup

  1. additionAfter addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 90 min
  4. temperaturecooled
  5. additionpoured carefully onto ice (200 ml)
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe extracts were washed (water (twice), brine),
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a dark oil
  11. customThe product was purified by flash chromatography
  12. washeluting with 7:3 hexane

Sources & evidence

ORD record
ord-4e708538b91446bf97466d297c1efd29
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

Loading…