Hydroxylamine → trans-4-Hepten-3-yl acetate
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
Procedure
A vial was charged with aminoalcohol A (0.0063 g, 0.026 mmol). To the vial was added 1.68 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 trans-4-hepten-3-yl acetate was formed 87% enantiomeric excess.
Sources & evidence
- ORD record
- ord-7682511bbd614705b0fbd621ccf044a6
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362344B1
Reaction notes
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