Hydrochloric Acid → HCID 57105694, compound

HRID 2211330Notes

Reaction equation

HRID 2211330 reaction equation
[CH3:1][C@@:2]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][C@H:3]2[CH2:9][C:10]#N.Cl.CC[O:15]CC>[H-].C([Al+]CC(C)C)C(C)C.CCCCCC>[CH3:1][C@@:2]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][C@H:3]2[CH2:9][CH:10]=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57299051HCID 57299051, compound

Product 1

HCID 57105694HCID 57105694, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21225700DiisobutylaluminumhydrideSolvent

Procedure

19.5 g (0.13M) of the nitrile (XI) obtained in 1-9) above was dissolved in 200 ml of absolute ether under a nitrogen gas stream and 160 ml of a 1M solution of diisobutylaluminum hydride in hexane was added dropwise thereto at room temperature. Then the resulting mixture was stirred for one hour, poured into ice/water and acidified with 1N hydrochloric acid. The organic phase was collected and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was distilled under reduced pressure to give 19.0 g (theoretical yield: 96%) of the aimed compound (XII) as a colorless oily material. b.p.: 45° to 47° C./0.5 mmHg.

Workup

  1. additionwas added dropwise
  2. customat room temperature
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporation of the solvent
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-cceca2137be44753ab4271327f23eff9
Source dataset
uspto-grants-1995_10
Patent number
US05463118

Reaction notes

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