Water → HCID 18973255, compound

HRID 2394397Notes

Reaction equation

HRID 2394397 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][N:20]1[C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([C:29](OC)=[O:30])[C:23]=2[CH:22]=[CH:21]1.O.[OH-].[Na+]>O1CCCC1>[OH:30][CH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[CH:22]=[CH:21][N:20]2[CH2:19][C:9]1[N:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:12][C:8]=1[CH3:7]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18973514HCID 18973514, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18973255HCID 18973255, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 114 mg of lithium aluminum hydride in 5 ml of tetrahydrofuran, there was dropwise added a solution obtained by dissolving, in 5 ml of tetrahydrofuran, 1.04 g of methyl 1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole-4-carboxylate prepared in Example 28 over 30 minutes, with ice-cooling and under an argon gas atmosphere. After stirring the reaction solution for one hour, there were, in order, added 0.11 ml of water, 0.11 ml of a 15% aqueous sodium hydroxide solution and 0.33 ml of water to the reaction solution, followed by stirring the mixture for 2 hours. The insolubles were filtered off, the resulting filtrate was concentrated and the residue was dried under reduced pressure to give 949 mg of 4-hydroxymethyl-1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole as colorless crystals. The yield thereof was found to be 99%.

Workup

  1. additionwas dropwise added a solution
  2. customobtained
  3. temperaturewith ice-cooling and under an argon gas atmosphere
  4. stirringby stirring the mixture for 2 hours
  5. filtrationThe insolubles were filtered off
  6. concentrationthe resulting filtrate was concentrated
  7. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-91148b20c4e2476991dcf8a558735a0c
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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