Hydroxylamine → HCID 22625133, compound

HRID 279407Notes

Reaction equation

HRID 279407 reaction equation
NO.[CH3:3][C:4]([CH3:8])([CH3:7])[CH:5]=[O:6].C([Zn][CH2:12][CH3:13])C.[C:14](OC(=O)C)(=[O:16])[CH3:15]>CCCCCC.C1(C)C=CC=CC=1.ClC1C=CC=CC=1>[C:14]([O:6][CH:5]([CH2:12][CH3:13])[C:4]([CH3:8])([CH3:7])[CH3:3])(=[O:16])[CH3:15]

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 7918Acetic AnhydrideHCID 12417PivalaldehydeHCID 178418750HCID 178418750, compound

Product 1

HCID 22625133HCID 22625133, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 7964ChlorobenzeneSolventHCID 8058HexaneSolvent

Procedure

A vial was charged with aminoalcohol 1 (0.0074 g, 0.026 mmol) prepared as in Example 1. To the vial was added 1.60 mL of a stock solution containing trimethylacetaldehyde (0.26 g), chlorobenzene internal standard (0.26 g), 1 M diethylzinc in hexane (6.0 mL), and toluene (3.0 mL). After 48 h, acetic anhydride (0.200 mL) was added. After an additional 72 h, a sample of the solution was analyzed by gas chromatography at 70° C. on a Cyclodex B stationary phase. The product 3-acetoxy-2,2-dimethylpentane was formed in 73% yield and 98% enantiomeric excess. The identity and yield of the product was established by comparison with an authentic sample prepared by treatment of racemic 2-methyl-3-pentanol with acetic anhydride.

Workup

  1. waitAfter an additional 72 h
  2. customwas analyzed by gas chromatography at 70° C. on a Cyclodex B stationary phase

Sources & evidence

ORD record
ord-56d35eb15f66481194bfaa09d997e6d0
Source dataset
uspto-grants-2002_03
Patent number
US06362344B1

Reaction notes

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