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

HRID 1671633Notes

Reaction equation

HRID 1671633 reaction equation
[C:1]([O:4][CH2:5][C:6](=[O:16])[CH2:7][C:8]1C=C[C:11](Cl)=[C:10](Cl)[CH:9]=1)(=[O:3])[CH3:2].ClCC(=O)CC1[S:22]C=CC=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[S:22][CH:11]=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 161000723-(3,4-Dichlorophenyl)-2-oxopropyl AcetateHCID 161002061-Chloro-3-(thiophen-2-yl)propan-2-one

Product 1

HCID 161000732-Oxo-3-(thiophen-2-yl)propyl acetateYield 13%

Procedure

The procedure described above for the synthesis of 3-(3,4-dichlorophenyl)-2-oxopropyl acetate was followed, reacting 1-chloro-3-(thiophen-2-yl)propan-2-one (1.00 g, 5.73 mmol) with acetic acid (0.66 mL, 0.69 g, 12 mmol) and triethylamine (1.60 mL, 1.16 g, 11.5 mmol). Purification by flash chromatography over silica gel (10-40% ethyl acetate in hexanes) gave an orange oil (0.144 g, 13% yield): 1H NMR (400 MHz, CDCl3) δ 2.17 (s, 3H) 3.95 (s, 2H) 4.74 (s, 2H) 6.92-6.94 (m, 1H) 6.99 (dd, J=5.2, 3.4 Hz, 1H) 7.25 (dd, J=5.1, 1.3 Hz, 1H).

Workup

  1. customPurification by flash chromatography over silica gel (10-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fd48ae02d3f24a3a8ddd9454eab5ffe9
Source dataset
uspto-grants-2011_08
Patent number
US07994333B2

Reaction notes

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