Sodium Hydroxide → HCID 22350904, compound

HRID 896448Notes

Reaction equation

HRID 896448 reaction equation
[CH2:1]([NH:8][C:9]([CH:11]1[CH2:20][CH:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].COCCO[Al+]OCCOC.[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][CH2:9][CH:11]1[CH2:20][CH:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 22350916HCID 22350916, compound

Product 1

HCID 22350904HCID 22350904, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 265 mg (0.66 mmol) of N-benzyl-4-(tert-butyldimethylsilanyloxy)-chroman-2-carboxamide in 2 ml of toluene is cooled in an ice bath, and 2 ml of sodium bis-(2-methoxyethoxy)aluminum dihydride (70% strength solution in toluene) are added. The reaction mixture is stirred at 60° C. for 2 hours and at room temperature overnight. 10 ml of 1 M aqueous sodium hydroxide solution are then added a little at a time, and the mixture is extracted with 20 ml of dichloromethane and again with 10 ml of dichloromethane. The combined organic phases are washed with 10 ml of water and evaporated to dryness. The product is obtained as an oily residue.

Workup

  1. extractionthe mixture is extracted with 20 ml of dichloromethane and again with 10 ml of dichloromethane
  2. washThe combined organic phases are washed with 10 ml of water
  3. customevaporated to dryness
  4. customThe product is obtained as an oily residue

Sources & evidence

ORD record
ord-44879cb03cf449f18b97c0d7ec8e3a69
Source dataset
uspto-grants-2005_07
Patent number
US06919360B2

Reaction notes

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