HCID 15486878, compound → HCID 15486879, compound

HRID 988231Notes

Reaction equation

HRID 988231 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH:15]=[C:14]([O:17][CH2:18][CH2:19][CH2:20][C:21](OCC)=[O:22])[CH:13]=[CH:12]2)(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[OH:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][CH:8]=[C:7]2[CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 15486878HCID 15486878, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15486879HCID 15486879, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 250 ml round-bottomed flask, the ester obtained in Step A (0.009 mol) is dissolved in 100 ml of anhydrous ether. 0.009 mol of lithium aluminium hydride is added in portions, and the reaction mixture is stirred for 6 hours at room temperature. The reaction mixture is then hydrolysed with a few drops of 1M NaOH, and the precipitate that forms is filtered off. The filtrate is dried over MgSO4 and evaporated under reduced pressure. The resulting residue is precipitated from an Et2O/petroleum ether mixture (1/1), suctioned off and recrystallised. White solid.

Workup

  1. filtrationhydrolysed with a few drops of 1M NaOH, and the precipitate that forms is filtered off
  2. dry with materialThe filtrate is dried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe resulting residue is precipitated from an Et2O/petroleum ether mixture (1/1)
  5. customrecrystallised

Sources & evidence

ORD record
ord-dbbad95d88674c10950d0fbb85604ea6
Source dataset
uspto-grants-2003_10
Patent number
US06635650B2

Reaction notes

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