Acetic Acid → 2-Oxo-3-(thiophen-3-yl)propyl Acetate

HRID 2375568Notes

Reaction equation

HRID 2375568 reaction equation
[C:1]([O:4][CH2:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12]C(Cl)=C(Cl)[CH:9]=1)(=[O:3])[CH3:2].ClCC(=O)CC1C=C[S:23]C=1.C(O)(=O)C.C(N(CC)CC)C>>[C:1]([O:4][CH2:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][S:23][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 161000723-(3,4-Dichlorophenyl)-2-oxopropyl AcetateHCID 161001782-Propanone, 1-chloro-3-(3-thienyl)-

Product 1

HCID 161000742-Oxo-3-(thiophen-3-yl)propyl AcetateYield 52%

Procedure

The procedure described above for the synthesis of 3-(3,4-dichlorophenyl)-2-oxopropyl acetate was followed, reacting 1-chloro-3-(thiophen-3-yl)propan-2-one (6.53 g, 37.4 mmol) with acetic acid (4.3 mL, 4.5 g, 75 mmol) and triethylamine (10.4 mL, 7.57 g, 74.8 mmol). Flash chromatography over silica gel (20% ethyl acetate in hexanes) gave pure product, a golden-yellow oil (3.85 g, 52% yield): 1H NMR (400 MHz, CDCl3) δ 2.16 (s, 3H) 3.77 (s, 2H) 4.70 (s, 2H) 6.98 (dd, J=4.8, 1.3 Hz, 1H) 7.14 (dd, J=1.8, 1.0 Hz, 1H) 7.32 (dd, J=4.9, 2.9 Hz, 1H).

Workup

  1. customFlash chromatography over silica gel (20% ethyl acetate in hexanes) gave pure product

Sources & evidence

ORD record
ord-0825ca0caf874f63b294841d5b8cb855
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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