Methanol → HCID 21288538, compound

HRID 868428Notes

Reaction equation

HRID 868428 reaction equation
[OH:1][CH:2]([C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#N)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].C([Al+]CC(C)C)C(C)C.C[OH:35].O>C1COCC1>[OH:1][CH:2]([C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:35])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14257786HCID 14257786, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 21288538HCID 21288538, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[[3-(1-hydroxyhexyl)phenoxy]methyl]benzonitrile (10.0 g). in THF was added diisobutylaluminum hydride (15 g.) and the reaction was refluxed overnight. Methanol (10.2 ml) was slowly added followed by water (5.7 ml). The mixture was filtered and the filtrate was concentrated to an oil. The oil was dissolved in chloroform. The solution was washed with 5% aqueous hydrochloride acid (4 times), dried (MgSO4) and concentrated to an oil (3.0 g., 30% yield). In like manner as above, using appropriate starting materials, the following intermediate was prepared:

Workup

  1. temperaturethe reaction was refluxed overnight
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated to an oil
  4. dissolutionThe oil was dissolved in chloroform
  5. washThe solution was washed with 5% aqueous hydrochloride acid (4 times)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to an oil (3.0 g., 30% yield)
  8. customthe following intermediate was prepared

Sources & evidence

ORD record
ord-cef4145375364afe87e86c300155e64b
Source dataset
uspto-grants-1988_10
Patent number
US04778931

Reaction notes

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