Acetonitrile → HCID 118108924, compound

HRID 716161Notes

Reaction equation

HRID 716161 reaction equation
C(#N)C.Cl.[CH3:5][O:6][NH2:7].[C:8]1([CH:14]2[O:18][CH:17](O)[CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.C(OCC)(=O)C.CCCCCC.C(N(CC)CC)C>[CH3:5][O:6][N:7]=[CH:17][CH2:16][CH2:15][CH:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:18]

Participants

8

Reactant 3

HCID 6342AcetonitrileHCID 521874O-Methylhydroxylamine hydrochlorideHCID 111163882-Furanol, tetrahydro-5-phenyl-

Product 1

HCID 118108924HCID 118108924, compoundYield 95.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

12 mL of acetonitrile, 6 mL of water and 1.0 g of O-methylhydroxylamine hydrochloride were added to 0.98 g of the 5-phenyloxolan-2-ol, and thereafter, 1.08 mL of triethylamine was added dropwise to the mixture. The thus obtained mixture was stirred at room temperature for 0.5 hours. Thereafter, hexane, ethyl acetate and water were added to the reaction mixture, and the water layer was then removed. The organic layer was dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure, so as to obtain 1.10 g of 4-(methoxyimino)-1-phenylbutan-1-ol in the form of a colorless oily product.

Workup

  1. customthe water layer was then removed
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationAfter that, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-0216562d95584f6f97f51e2f82b3412a
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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