1-Bromohexane → HCID 22559392, compound

HRID 984546Notes

Reaction equation

HRID 984546 reaction equation
[C:1]([O:5][C:6](=[O:15])[CH:7]([O:11][C:12](=[O:14])[CH3:13])[C:8]([CH3:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CN(C=O)C>[C:1]([O:5][C:6](=[O:15])[C:7]([O:11][C:12](=[O:14])[CH3:13])([C:8](=[O:9])[CH3:10])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 11736056Tert-butyl 2-acetoxyacetoacetate

Product 1

HCID 22559392HCID 22559392, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the general alkylation method, tert-butyl-2-acetoxy-aceto-acetate (219a) (1.08 g, 5.00 mmol), NaH (156 mg, 6.5 mmol) and hexylbromide (702 μL, 825 mg, 5.00 mmol) were reacted in DMF (10 mL) to give 2-acetoxy-2-acetyl-octanoic-acid-tert-butylester (250k) (1063 mg, 3.54 mmol, 71%) as a slightly yellow oil. Then, 250k (2.19 g, 7.29 mmol) and 139 mg (0.73 mmol) p-TsOH.H2O were stirred in 22.0 mL benzene according to decarboxylation method A. Kugelrohr distillation at 0.8 mbar and 80° C. and subsequent flash-chromatography (column dimensions: 2.0×20.0 cm, diethylether/petroleum ether=1:6) gave 251k (419 mg 2.10 mmol, 29%) as a colorless oil.

Sources & evidence

ORD record
ord-fff45d8fbe184bb69f7d49088935714e
Source dataset
uspto-grants-2005_03
Patent number
US06867333B2

Reaction notes

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