Nitrogen → 1H-indol-4-ylmethanol

HRID 2100341Notes

Reaction equation

HRID 2100341 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10](OC)=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].N#N>O1CCCC1>[OH:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2

Participants

5

Reactant 3

HCID 947NitrogenHCID 2733668methyl 1H-indole-4-carboxylate2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 27734571H-indol-4-ylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 25 g of methyl 4-indolecarboxylate (1) in 200 ml of tetrahydrofuran is added to a suspension of LiAlH4 in 100 ml of tetrahydrofuran under a protective-gas atmosphere (N2) at such a rate that the temperature of the reaction mixture does not exceed 40° C. When the addition is complete, the reaction mixture is stirred at room temperature (25° C.) for approximately two further hours until the methyl 4-indolecarboxylate has reacted completely. The reaction mixture is subsequently hydrolysed by addition of ice-water (about 100 ml), and the hydrolysate is filtered through a bed of kieselguhr. After the tetrahydrofuran has been removed by distillation, the aqueous phase obtained is extracted with ethyl acetate. The organic phase obtained is dried over magnesium sulfate and evaporated, giving 16.0 g (76% of theory) of a pale-beige crystalline residue of 4-hydroxymethylindole (2).

Workup

  1. customdoes not exceed 40° C
  2. additionWhen the addition
  3. customhas reacted completely
  4. filtrationthe hydrolysate is filtered through a bed of kieselguhr
  5. customAfter the tetrahydrofuran has been removed by distillation
  6. customthe aqueous phase obtained
  7. extractionis extracted with ethyl acetate
  8. customThe organic phase obtained
  9. dry with materialis dried over magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-226acb6b769249d0b03a809cedf90b8f
Source dataset
uspto-grants-2009_08
Patent number
US07572796B2

Reaction notes

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