Water → HCID 57675741, compound

HRID 2264706Notes

Reaction equation

HRID 2264706 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[N:13]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][CH:24]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2)=O)C.O.[OH-].[Na+]>O1CCCC1>[CH2:30]([O:29][C:26]1[CH:27]=[CH:28][C:23]([N:13]2[C:14]3[C:19](=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=3)[CH:20]=[C:12]2[CH2:10][OH:9])=[CH:24][CH:25]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57675736HCID 57675736, compound

Product 1

HCID 57675741HCID 57675741, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.53 mL, 1 M in tetrahydrofuran, 1.53 mmol) was diluted with tetrahydrofuran (5 mL) under N2, and 1-(4-benzyloxyphenyl)-5-methoxy-1H-indole-2-carboxylic acid ethyl ester (0.51 g, 1.27 mmol) in tetrahydrofuran (5 mL) was added dropwise. The reaction was stirred at reflux for 2 hours, then cooled to room temperature. Water (0.3 mL) was added carefully, followed by 2 N NaOH (0.3 mL) and water (0.9 mL). The solvent was evaporated, and the residue was partitioned between water and ethyl acetate. The organic was separated, dried over MgSO4, and concentrated to give 0.41 g (88% yield) of crude product. LC-MS (C23H21NO3 calc'd 359) m/z 360 (M+H).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe organic was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e5d4dd3ba5fd4f45a52b77eb30ef08ee
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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