Ethyl Acetate → HCID 12467033, compound

HRID 1646757Notes

Reaction equation

HRID 1646757 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[NH:12][C:13]2[C:18]([C:19]=1[CH2:20][CH3:21])=[CH:17][CH:16]=[CH:15][CH:14]=2)=O.C(OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1.CO>[CH2:20]([C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[CH2:9][OH:8])[CH3:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 22961117HCID 22961117, compound

Product 1

HCID 12467033HCID 12467033, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the suspension of lithium aluminum hydride (4.15 g) in tetrahydrofuran (41 ml) at 15°-30° C. under a nitrogen atmosphere was added dropwise over 45 minutes 3-ethyl-2-indolecarboxylic acid methyl ester (22.2 g) in tetrahydrofuran. After the mixture was stirred at room temperature for an hour, ethyl acetate (200 ml) was added dropwise at 20°-30° C., followed by the addition of methanol (10 ml) at the same temperature. The reaction mixture was treated with saturated aqueous potassium sodium tartrate solution (150 ml). Separated organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (10% ethylacetate-n-hexane) to give 3-ethyl-2-hydroxymethylindole (14.0 g) as crystals.

Workup

  1. dry with materialSeparated organic layer was dried over anhydrous magnesium sulfate
  2. customevaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (10% ethylacetate-n-hexane)

Sources & evidence

ORD record
ord-6e07491302ef41208165d3dc71d18ba2
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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