Hydrochloric Acid → HCID 19082133, compound

HRID 265299Notes

Reaction equation

HRID 265299 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]#N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH2:27].Cl>O1CCCC1>[C:11]1([CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH:25]=[O:27])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 19082234HCID 19082234, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19082133HCID 19082133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminum hydride (3.3 ml, 1.5M in toluene) was added dropwise to a cooled (0°) stirred solution of 3-[2-[2-phenylethoxy]ethoxy]propanenitrile (1.0 g) from step a) in tetrahydrofuran. After 30 min the mixture was warmed to room temperature and stirred for a further 2 hours. Water and 10% aqueous hydrochloric acid were added cautiously and the reaction stirred for a further 5 min. The reaction was extracted several times with ether and the combined ethereal extracts were washed with saturated aqueous sodium bicarbonate solution and brine, dried (MgSO4) and evaporated under reduced pressure to yield the subtitled compound as a yellow oil. The material was used in the next step without purification.

Workup

  1. temperaturea cooled (0°)
  2. stirringthe reaction stirred for a further 5 min
  3. extractionThe reaction was extracted several times with ether
  4. washthe combined ethereal extracts were washed with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-905c4d8937ed4d999058432fb0105f4d
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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