Sodium Hydroxide → HCID 19921640, compound

HRID 1647791Notes

Reaction equation

HRID 1647791 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([Si](C)(C)C)=[C:7]2[CH2:17][CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)(=[O:3])[CH3:2].[OH-].[Na+]>C(#N)C>[NH4+:9].[OH-:3].[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:17][CH2:18][CH2:19][OH:20])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19921651HCID 19921651, compound

Product 2

HCID 14923Ammonium HydroxideHCID 19921640HCID 19921640, compoundYield 167.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5-acetyl-3-[3-(t-butyldimethylsiloxy)propyl]-2-trimethylsily 1-1H-indole (1.8 g, 5 mmol) in acetonitrile (100 mL) was added a 50% HF solution (4 mL) After stirring for 24 h at 23° C., the reaction was made basic (pH 10) by the addition of 50% NaOH solution and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated NaCl and next with water. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (CH2Cl2 :MeOH:NH4OH; 95:5:0.5) of the concentrate afforded 1-[5-acetyl1H-indol-3-yl]-3-propanol (0.91 g, 94%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaCl and next with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19b05ee46bf44adfa06fc28de04290d9
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

Loading…