Benzaldehyde → 2-Methyl-1-phenylbut-3-en-1-ol
Reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C([C:10]([OH:19])([CH:15]([CH3:18])[CH:16]=[CH2:17])[C:11]([CH3:14])([CH3:13])C)(C)(C)C.C(=O)C1C=CC=CC=1.C(OCC)C>CCCCC.C1COCC1.[Cl-].[Cl-].[Zn+2]>[CH3:18][CH:15]([CH:16]=[CH2:17])[CH:10]([C:11]1[CH:13]=[CH:3][CH:2]=[CH:1][CH:14]=1)[OH:19]Participants
8
Procedure
1.58 ml of a 1.6-molar solution of n-butyllithium (2.52 mmol) in pentane were added dropwise at −78° C. under argon for 5 minutes to a stirred solution of 500 mg (2.52 mmol) 3-tert-butyl-2,2,4-trimethylhex-5-en-3-ol in 4 ml THF. The solution obtained was stirred for 15 minutes, then 256 μl (2.52 mmol) benzaldehyde and subsequently for 3 minutes a solution of 343 mg (2.52 mmol) ZnCl2 in 2 ml THF were added. The reaction mixture was stirred for 1 hour at −78° C. and then heated to room temperature. Subsequently it was processed analogous to Example 1. The raw product obtained was cleaned by means of a silica column with 10% diethyl ether/light gasoline. There was obtained the alcohol as a pale-yellow oil.
Workup
- customThe solution obtained
- stirringThe reaction mixture was stirred for 1 hour at −78° C.
- customThe raw product obtained
Sources & evidence
- ORD record
- ord-8abd42a7b9f94df4bb4d76a2bbb594d0
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291713B1
Reaction notes
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