Methyl acetoacetate → Methyl 3-oxo-7,11,15-trimethylhexadeca-6,10,14-trienoate
Reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:11](Br)[CH:12]=[C:13]([CH2:15][CH2:16][CH:17]=[C:18]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH3:19])[CH3:14]>C1COCC1.CCCCCC>[O:4]=[C:3]([CH2:5][CH2:11][CH:12]=[C:13]([CH3:14])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:19])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH2:2][C:1]([O:7][CH3:8])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Methyl acetoacetate (225 μL, 2.1 mmol) was added dropwise to a stirred suspension of sodium hydride (50% oil suspension, prewashed with hexane) (100 mg, 2.1 mmol) in anhydrous THF (5 mL) at 0° C. under an Argon atmosphere. The resulting solution was stirred 15 minutes at 0° C. and then treated with a 1.6M solution (1.3 mL, 2.1 mmol) of n-butylithium in hexane over 2 minutes. The yellow solution was stirred 15 min at 0° C. and then treated dropwise with farnesyl bromide (545 μL, 2.0 mmol). The cloudy orange solution was stirred at 20° C. for 11/2 hours and then quenched by dropwise addition of saturated aqueous NH4Cl solution. The resulting mixture was diluted with ethyl acetate and washed with water, dried, filtered and evaporated to give the crude product which was used in the next step without purification.
Workup
- stirringThe yellow solution was stirred 15 min at 0° C.
- stirringThe cloudy orange solution was stirred at 20° C. for 11/2 hours
- customquenched by dropwise addition of saturated aqueous NH4Cl solution
- additionThe resulting mixture was diluted with ethyl acetate
- washwashed with water
- customdried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-a5a8a985beb948b38bfd0eccdaaad963
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05362906
Reaction notes
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