Acetyl chloride → 2-Methylbenzofuran-6-yl acetate

HRID 1825185Notes

Reaction equation

HRID 1825185 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6]=[C:7]([CH3:9])[O:8][C:4]=2[CH:3]=1.[C:12](Cl)(=[O:14])[CH3:13].C(N(CC)CC)C.C(OC1C=CC2C=C(C)SC=2C=1)(=O)C>>[C:12]([O:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6]=[C:7]([CH3:9])[O:8][C:4]=2[CH:3]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 122034982-Methylbenzofuran-6-olHCID 22143532HCID 22143532, compound

Product 1

HCID 221435562-Methylbenzofuran-6-yl acetateYield 101.3%

Procedure

This material was prepared from 6-hydroxy-2-methylbenzofuran (654 mg, 4.41 mmole) by treatment with acetyl chloride (0.41 ml, 5.74 mmole) and triethylamine (0.74 ml, 5.30 mmole) in a manner as previously described for 8b to give the desired product as an oil (850 mg, ˜quant). 1H NMR (CDCl3) δ 7.41 (1H, d, J=8.3 Hz), 7.13 (1H, s), 6.88 (1H, dd, J=8.3, 1.9 Hz), 6.32 (1H, s), 2.42 (3H, s), 2.30 (3H, s).

Sources & evidence

ORD record
ord-7f31596760d84cc6954b7dfd9dccfbc0
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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