Tetrahydrofuran → HCID 21405638, compound

HRID 1973148Notes

Reaction equation

HRID 1973148 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][C:13]1[C:14]([CH3:25])=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([C:22](O)=[O:23])=[CH:16]2>O>[Cl:12][C:13]1[C:14]([CH3:25])=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH2:22][OH:23])=[CH:16]2

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 2139633350536-61-3

Product 1

HCID 21405638HCID 21405638, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

240 ml. anhydrous tetrahydrofuran and 3.5 g. lithium aluminium hydride were placed in a 1 liter three-necked flask equipped with a stirrer, dropping funnel and reflux condenser provided with a calcium chloride tube. A solution of 6.5 g. 5-chloro-4-methyl-indole-2-carboxylic acid in 100 ml. anhydrous tetrahydrofuran was then slowly added thereto dropwise, while stirring at ambient temperature, whereafter the reaction mixture was heated to 50° C. for 2 hours. After cooling, 4.7 ml. water were added very slowly and carefully thereto dropwise and precipitated inorganic compounds were filtered off with suction and then thoroughly washed with tetrahydrofuran. The combined solutions were evaporated and the oily residue was dissolved in a little diethyl ether, mixed with ligroin and, after rubbing with a glass rod, brought to crystallization. There were thus obtained 3.6 g. (59% of theory) 5-chloro-4-methyl-2-hydroxymethyl -indole which can be recrystallized from toluene, with the use of active charcoal. The product had a melting point of 108° C.

Workup

  1. customequipped with a stirrer
  2. temperaturereflux condenser
  3. customprovided with a calcium chloride tube
  4. temperaturewas heated to 50° C. for 2 hours
  5. temperatureAfter cooling
  6. customcarefully thereto dropwise and precipitated inorganic compounds
  7. filtrationwere filtered off with suction
  8. washthoroughly washed with tetrahydrofuran
  9. customThe combined solutions were evaporated
  10. dissolutionthe oily residue was dissolved in a little diethyl ether
  11. additionmixed with ligroin
  12. custombrought to crystallization
  13. custom(59% of theory) 5-chloro-4-methyl-2-hydroxymethyl -indole which can be recrystallized from toluene, with the use of active charcoal

Sources & evidence

ORD record
ord-303afc7dd8d74a6380af8090b57d30e8
Source dataset
uspto-grants-1976_12
Patent number
US03996241

Reaction notes

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