Sodium Hydroxide → HCID 967125, compound

HRID 1716852Notes

Reaction equation

HRID 1716852 reaction equation
[N:1]1([CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+]>CO.C1COCC1>[N:1]1([CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3399806HCID 3399806, compound

Product 1

HCID 967125HCID 967125, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 4-(1H-indol-1-ylmethyl)benzoate (9.05 g; 34 mmol) was dissolved in MeOH/THF (1:1), treated with sodium hydroxide (1.36 g, 34 mmol) stirred at room temperature overnight and concentrated under reduced pressure. The resultant concentrate was diluted with 1N sodium hydroxide (50 mL), washed with EtOAc, acidified with concentrated HCl and extracted with EtOAc. The combined extracts were dried over MgSO4 and concentrated to dryness to give the title product in 77% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 250 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationThe resultant concentrate
  3. additionwas diluted with 1N sodium hydroxide (50 mL)
  4. washwashed with EtOAc
  5. extractionextracted with EtOAc
  6. dry with materialThe combined extracts were dried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e0600cdb1be9447891c095f1b0114ec2
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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