Dicyclohexylcarbodiimide → 2-(2-Cyclopropylacetyl)-5,5-dimethylcyclohexane-1,3-dione

HRID 1875405Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH2:3]1.[CH:11]1([CH2:14][C:15](O)=[O:16])[CH2:13][CH2:12]1.C1(N=C=NC2CCCCC2)CCCCC1.C1(=O)CCCCC1=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:11]1([CH2:14][C:15]([CH:5]2[C:6](=[O:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]2=[O:9])=[O:16])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

5,5-Dimethyl-1,3-cyclohexanedione (1.051 g, 7.5 mmol, 1.5 eq), cyclopropylacetic acid (500.6 mg, 5.0 mmol), and 4-dimethylaminopyridine (916.3 mg, 7.5 mmol, 1.5 eq) were dissolved in 10 mL of CH2Cl2, cooled to 0° C. in an ice bath. A solution of N,N′-dicyclohexylcarbodiimide (1.238 g, 16.0 mmol, 1.2 eq) in 5 mL of CH2Cl2 was added dropwise over two minutes to the cyclohexanedione solution. The reaction mixture was then stirred at 0° C. for 10 minutes and at room temperature for 16 hours. The reaction mixture was then filtered and the filtrate purified by column chromatography (hexane to 30% EtOAc/hexane) to yield 1.022 g (92% yield) 2-(2-Cyclopropyl-acetyl)-5,5-dimethyl-cyclohexane-1,3-dione as a pale yellow oil.

Workup

filtrationThe reaction mixture was then filtered
customthe filtrate purified by column chromatography (hexane to 30% EtOAc/hexane)

Sources & evidence

ORD record: ord-43ca7cbb7d94486aac75cac1ee74015d
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309548B2

Reaction notes

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