Hydroxylamine → HCID 22625133, compound

HRID 635447Notes

Reaction equation

HRID 635447 reaction equation
NO.Cl[C:4]1[CH:9]=[CH:8]C=CC=1.C([Zn][CH2:13][CH3:14])C.[C:15]([O:18][C:19](=O)C)(=[O:17])[CH3:16].[CH3:22]CCCCC>C1(C)C=CC=CC=1>[C:15]([O:18][CH:19]([CH2:13][CH3:14])[C:9]([CH3:8])([CH3:4])[CH3:22])(=[O:17])[CH3:16]

Participants

7

Reactant 5

HCID 787HydroxylamineHCID 7918Acetic AnhydrideHCID 7964ChlorobenzeneHCID 8058HexaneHCID 178418750HCID 178418750, compound

Product 1

HCID 22625133HCID 22625133, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A vial was charged with aminoalcohol A (0.0061 g, 0.025 mmol) prepared as in Example 13. To the vial was added 1.63 mL of a stock solution containing trimetbylacetaldehyde (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 57% yield and 97% enantiomeric excess. The identity and yield of the product was established by comparison with an authentic sample prepared by treatment of racemic 2,2-dimethyl-3-pentanol with acetic anhydride.

Workup

  1. customA (0.0061 g, 0.025 mmol) prepared as in Example 13

Sources & evidence

ORD record
ord-a661666f213d4240a0e0a7a21ca3b6e7
Source dataset
uspto-grants-2001_02
Patent number
US06187918B1

Reaction notes

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