Sodium Hydroxide → HCID 59087958, compound

HRID 656278Notes

Reaction equation

HRID 656278 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:12]=[CH:13][C:14]([C:21]#[N:22])=[C:15]([CH:20]=1)[C:16](OC)=[O:17])([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+]>CCOCC>[NH2:22][CH2:21][C:14]1[CH:13]=[CH:12][C:11]([C:7]([CH3:8])([CH3:10])[CH3:9])=[CH:20][C:15]=1[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69118297HCID 69118297, compound

Product 1

HCID 59087958HCID 59087958, compoundYield 256.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (105 mg) was supended in ether (3 ml) and the suspension was cooled to 0° C. To the suspension was added dropwise a solution of the compound 13-6 (140 mg) prepared by Step 2 in ether (4 ml) and the mixture was refluxed for 2 hours. After the completion of the reaction, the reaction mixture was basified with 5 N aqueous sodium hydroxide solution, followed by adding aqueous Rochel solution thereto and then stirring for 1 hour. Then, the resulting mixture was extracted with ether (50 ml×3) and concentrated under reduced pressure to yield the compound 13-7 (320 mg, 90%). The following Step 4 was proceeded using the compound 13-7 which was not purified

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customAfter the completion of the reaction
  3. additionby adding aqueous Rochel solution
  4. extractionThen, the resulting mixture was extracted with ether (50 ml×3)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-758c4f10cf214b1691514ab495dcc44e
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

Loading…