Hydrochloric Acid → (3-Benzyl-1H-indol-1-yl)acetaldehyde

HRID 654470Notes

Reaction equation

HRID 654470 reaction equation
[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][C:18](OC)=[O:19])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CO.Cl>C1(C)C=CC=CC=1.O>[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH:18]=[O:19])[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 54285481HCID 54285481, compound

Product 1

HCID 54560454(3-Benzyl-1H-indol-1-yl)acetaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
-65 °C

Procedure

To a solution of the product from Step 1 (470 mg, 1.68 mmol) in toluene (15 mL) at -65° C. there was slowly added 1.0M DIBAL in toluene (2.24 mL, 2.24 mmol) and the mixture was stirred at -65° C. for 1 hour. There was slowly added MeOH (5 mL) and the mixture was then allowed to warm up to r.t. There was added H2O (20 mL) and 1N aqueous HCl (10 mL) and after shaking the organic phase was washed with H2O, dried over MgSO4 and evaporated down to an oily residue which was taken as such to the next step.

Workup

  1. customat -65° C.
  2. temperatureto warm up to r.t
  3. stirringafter shaking the organic phase
  4. washwas washed with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated down to an oily residue which

Sources & evidence

ORD record
ord-71610082909d45b593f439a4d0229de7
Source dataset
uspto-grants-1992_07
Patent number
US05132319

Reaction notes

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