Water → HCID 21087563, compound

HRID 348520Notes

Reaction equation

HRID 348520 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH2:21][CH3:22])[C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=3)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:21]([N:10]1[C:9]2[CH:8]=[CH:7][C:6]([CH2:4][OH:3])=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH3:22]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66720186HCID 66720186, compound

Product 1

HCID 21087563HCID 21087563, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9-ethyl-6-methoxycarbazole-3-carboxylic acid ethyl ester (1.36 g, 4.58 mmol) in anhydrous THF was added to a solution of lithium aluminum hydride in THF (25 mL) at 0° C. The reaction was stirred for 1 hour then water (1 mL) was added followed by 2M NaOH (1 mL) and finally water (1 mL). The reaction was then filtered on diatomaceous earth and the filtrate was dried and solvent removed in vacuo to afford 0.79 g of the crude alcohol.

Workup

  1. filtrationThe reaction was then filtered on diatomaceous earth
  2. customthe filtrate was dried
  3. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-9bc2d27146c14b3aa5e3d30abe7e164a
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

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