Water → HCID 53950270, compound

HRID 581923Notes

Reaction equation

HRID 581923 reaction equation
CC(C[AlH]CC(C)C)C.[C:10]([C:12]1[CH:32]=[CH:31][C:15]2[N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[N:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH:20]=3)[CH:17]=[N:18][C:14]=2[CH:13]=1)#N.C(Cl)Cl.[NH4+].[Cl-].[OH2:38]>C1(C)C=CC=CC=1>[CH:10]([C:12]1[CH:32]=[CH:31][C:15]2[N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[N:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH:20]=3)[CH:17]=[N:18][C:14]=2[CH:13]=1)=[O:38]

Participants

7

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 54158492HCID 54158492, compound

Product 1

HCID 53950270HCID 53950270, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of DIBAL-H in toluene (2.5 ml, 1.0 M) was added to a mixture of (67) (367 mg, 1.2 mmol) and CH2Cl2 (60 ml) at -78° C. The reaction mixture was stirred for 1 hr at -78° C. and for 1 hr at room temperature. A saturated NH4Cl solution was added to the reaction mixture and stirring was continued for 0.5 hr. The mixture was poured into water and extracted with CH2Cl2. The organic extract was dried over MgSO4, and the solvent was evaporated under reduced pressure to give (68) (142 mg, 38%).

Workup

  1. stirringstirring
  2. waitwas continued for 0.5 hr
  3. extractionextracted with CH2Cl2
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f5805b365dcc44ca9357b7a3fcc447df
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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