Acetic Acid → 3-(5-Chlorobenzo[b]thiophen-3-yl)-2-oxopropyl acetate

HRID 1671645Notes

Reaction equation

HRID 1671645 reaction equation
[C:1]([O:4]CC(=O)CC1C=CC(Cl)=C(Cl)C=1)(=[O:3])[CH3:2].Cl[CH2:18][C:19](=[O:31])[CH2:20][C:21]1[C:22]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:23]=2[S:24][CH:25]=1.C(O)(=O)C.C(N(CC)CC)C>>[C:1]([O:4][CH2:18][C:19](=[O:31])[CH2:20][C:21]1[C:22]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:23]=2[S:24][CH:25]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 161000723-(3,4-Dichlorophenyl)-2-oxopropyl AcetateHCID 161001811-Chloro-3-(5-chlorobenzo[b]thiophen-3-yl)-propan-2-one

Product 1

HCID 161000613-(5-Chlorobenzo[b]thiophen-3-yl)-2-oxopropyl acetateYield 57%

Procedure

The procedure described above for the synthesis of 3-(3,4-dichlorophenyl)-2-oxopropyl acetate was followed, reacting 1-chloro-3-(5-chlorobenzo[b]thiophen-3-yl)-propan-2-one (4.43 g, 17.1 mmol) with acetic acid (2.0 mL, 2.1 g, 35 mmol) and triethylamine (4.9 mL, 3.6 g, 35 mmol). Flash chromatography over silica gel (20% ethyl acetate in hexanes) gave pure product, a pale yellow solid (2.76 g, 57% yield): 1H NMR (400 MHz, CDCl3) δ2.16 (s, 3H) 3.94 (d, J=1.0 Hz, 2H) 4.73 (s, 2H) 7.34 (ddd, J=8.6, 2.0, 0.5 Hz, 1H) 7.39-7.42 (m, 1H) 7.65 (d, J=2.0 Hz, 1H) 7.78 (dd, J=8.6, 0.5 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-ebbbaaf83cb04bae99b5610e23ad7e14
Source dataset
uspto-grants-2011_08
Patent number
US07994333B2

Reaction notes

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