1-Chloropinacolone → Ethyl 2-acetyl-5,5-dimethyl-4-oxohexanoate

HRID 642240Notes

Reaction equation

HRID 642240 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([CH2:9][C:10]([C:12]1[CH:17]=CC(F)=C[CH:13]=1)=[O:11])[C:6](=[O:8])[CH3:7])[CH3:2].Cl[CH2:21]C(=O)C(C)(C)C>>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([C:6](=[O:8])[CH3:7])[CH2:9][C:10](=[O:11])[C:12]([CH3:13])([CH3:17])[CH3:21])[CH3:2]

Participants

3

Reactant 2

HCID 835721-ChloropinacoloneHCID 141739732-Acetyl-4-(4-fluorophenyl)-4-oxobutyric acid ethyl ester

Product 1

HCID 11775940Ethyl 2-acetyl-5,5-dimethyl-4-oxohexanoate

Procedure

Prepared in analogy to that of 2-[2-(4-fluoro-phenyl)-2-oxo-ethyl]-3-oxo-butyric acid ethyl ester from 1-chloro-3,3-dimethyl-butan-2-one. The title compound, 1H NMR (200 MHz, CDCl3): δ (ppm)=4.19 (q, 2H, J=7.2 Hz), 4.02 (m, 1H), 3.23 (dd, 1H, J=8.2 Hz, 18.4 Hz), 3.00 (dd, J=6.0 Hz, J=18.4 Hz), 2.37 (s, 3H), 1.8 (t, 3H, J=7.2 Hz), 1.17 (s, 9H).

Sources & evidence

ORD record
ord-45519a9c31844280b2c2d4d28e6c878e
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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