Hydrochloric Acid → HCID 19787148, compound

HRID 1646756Notes

Reaction equation

HRID 1646756 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][CH:15]=[CH2:16])=[CH:11][CH:10]=[CH:9][CH:8]=2)=O.[BH4-].[Li+].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH2:14]([C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH2:3][OH:2])[CH:15]=[CH2:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 54163397HCID 54163397, compound

Product 1

HCID 19787148HCID 19787148, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 3-allyl-2-indolecarboxylic acid methyl ester (13.1 g) and lithium borohydride (2.65 g) in tetrahydrofuran (100 ml) was refluxed for 3 hours. After cooling, the reaction mixture was diluted with chilled water, made acidic with 2N-hydrochloric acid. The mixture was neutralized with aqueous sodium bicarbonate solution and extracted twice with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give 3-allyl-2-hydroxymethylindole (11.2 g) as an oil. The oil was used in the next reaction without further purification.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionextracted twice with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-59c1e3a688fb4bbfac322a30cae3b249
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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