Hydrochloric Acid → HCID 22062805, compound

HRID 2120597Notes

Reaction equation

HRID 2120597 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:16][CH:15]=2)=O)C.O.Cl>C1COCC1>[C:21]1([C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12]([CH2:10][OH:9])=[CH:20]3)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12404978Ethyl 5-phenyl-1H-indole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 22062805HCID 22062805, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1M Lithium aluminum hydride in THF was added to a cooled solution of 5-phenyl-1H-indole-2-carboxylic acid ethyl ester 44 (0.375 g, 1.41 mmole) in dry THF (5 ml). After 2 hrs at room temperature, the excess reagent was decomposed with water, acidified with 1M HCl, extracted, washed, dried, and evaporated to give about 0.285 g of (5-phenyl-indol-2-yl)-methanol 45, mp. 115-116° C.

Workup

  1. extractionextracted
  2. washwashed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-6e1b01de75294a2590d421f15e6e12f7
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Reaction notes

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