Acetyl chloride → 2-Ethyl-1-benzothiophen-6-yl acetate

HRID 985339Notes

Reaction equation

HRID 985339 reaction equation
[CH2:1]([C:3]1[S:7][C:6]2[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:5]=2[CH:4]=1)[CH3:2].[C:13](Cl)(=[O:15])[CH3:14].CCN(CC)CC>>[C:13]([O:12][C:9]1[CH:10]=[CH:11][C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[S:7][C:6]=2[CH:8]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 221435082-Ethyl 6-hydroxybenzo[b]thiophene

Product 1

HCID 221435142-Ethyl-1-benzothiophen-6-yl acetateYield 147.8%

Procedure

This material was prepared by treatment of 2-ethyl-6-hydroxybenzo[b]thiophene 134b (1.60 g, 9 mmole) with acetyl chloride (1 ml, 1.10 g, 14 mmole) and Et3N (2 ml, 1.45 g, 14 mmole) in a manner as previously described for example 8b to give a white solid (2.93 g, 93%). 1H NMR (DMSO-d6) δ7.72 (1H, d, J=8.5 Hz), 7.68 (1H, d, J=2.2 Hz), 7.15 (1H, s), 7.08 (1H, dd, J=2.2, 8.5 Hz), 2.89 (2H, q, J=7.5 Hz), 2.28 (3H, s), 1.29 (3H, t, J=7.5 Hz).

Sources & evidence

ORD record
ord-2e0d3aed1ac54122b9aed33710fe764f
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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