Hydroxylamine → trans-4-Hepten-3-yl acetate

HRID 279409Notes

Reaction equation

HRID 279409 reaction equation
NO.C(=O)/C=C/CC.[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C.C([Zn]CC)C.[C:24]([O:27]C(=O)C)(=[O:26])[CH3:25]>CCCCCC.C1(C)C=CC=CC=1>[C:24]([O:27][CH:16](/[CH:17]=[CH:18]/[CH2:13][CH3:9])[CH2:15][CH3:14])(=[O:26])[CH3:25]

Participants

8

Reactant 5

HCID 787HydroxylamineHCID 7366Tert-ButylbenzeneHCID 7918Acetic AnhydrideHCID 5364752(E)-2-PentenalHCID 178418750HCID 178418750, compound

Product 1

HCID 22625128trans-4-Hepten-3-yl acetate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A vial was charged with aminoalcohol 1 (0.0032 g, 0.011 mmol) prepared as in Example 1. To the vial was added 1.62 mL of a stock solution containing trans-2-pentenal (0.34 g), t-butylbenzene internal standard (0.25 g), 1 M diethylzinc in hexane (8.0 mL), and toluene (4.0 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 80° C. on a Cyclodex B stationary phase. The product trans4hepten-3-yl acetate was formed 85% enantiomeric excess.

Workup

  1. waitAfter an additional 72 h
  2. customwas analyzed by gas chromatography at 80° C. on a Cyclodex B stationary phase

Sources & evidence

ORD record
ord-1cc1fcedbb564f0aa8748dd9ffd9be19
Source dataset
uspto-grants-2002_03
Patent number
US06362344B1

Reaction notes

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