Acetophenone → 1-(Phenyl)-1,3-heptanedione

HRID 2300600Notes

Reaction equation

HRID 2300600 reaction equation
[C:1]1([C:7](=[O:13])[CH2:8][C:9](=[O:12])[CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](C1C=CC=CC=1)(=O)[CH3:15].C(OCC)(=O)CCCC>>[C:1]1([C:7](=[O:13])[CH2:8][C:9](=[O:12])[CH2:10][CH2:11][CH2:14][CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 7410AcetophenoneHCID 10882Ethyl valerateHCID 21408Propionyl Acetophenone

Product 1

HCID 4365851-(Phenyl)-1,3-heptanedione

Procedure

The title compound was prepared (as described above for Intermediate 16) from 2.2 g (18.3 mmol) of acetophenone and 4.51 g (35 mmol) of ethyl valerate to yield 2.6 grams of Intermediate 18:: TLC Rf=0.52 (1/9 EtOAc/Hexanes); 1H NMR (400 MHz, CDCl3) δ7.87 (m, 2H), 7.48 (m, 3H), 6.17 (s,1H), 2.42 (t, 2H, J=7.6), 1.67 (m, 2H), 1.4 (m, 2H), 0.95 (t, 3H, J=7.2); low resolution MS (ES+)m/e 205.1 (MH+), 227.1 (M+Na+).

Sources & evidence

ORD record
ord-77e89998a0b34127b60edeed88244948
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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