Methanesulfonic Acid → HCID 18955530, compound

HRID 2380390Notes

Reaction equation

[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C([C:12]1[CH:13]=[C:14](C(C)(C)C)[C:15]2[O:19][C:18](=[O:20])[CH:17]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=3)[C:16]=2[CH:30]=1)(C)(C)C.CS(O)(=O)=[O:37]>C1(C)C(C)=CC=CC=1>[CH2:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([CH:17]2[C:16]3[CH:30]=[C:12]([O:37][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[CH:13]=[CH:14][C:15]=3[O:19][C:18]2=[O:20])=[CH:22][CH:23]=1)[CH3:29]

Participants

Conditions

Temperature: 95 °C

Procedure

2.41 g (20.0 mmol) of pivaloyl chloride are added dropwise over a period of 10 minutes to a suspension of 2.70 g (10.0 mmol) of 3-(4-ethoxyphenyl)-5-hydroxybenzofuran-2-one (compound (136), Table 1, Example 1) in 10 ml of xylene and 0.1 ml of methanesulfonic acid which is stirred at 95° C. under a nitrogen atmosphere. The clear, homogeneous reaction mixture is then refluxed for 2.5 hours and then concentrated under a slight vacuum. The residue is taken up in dichloromethane and washed with saturated sodium bicarbonate solution and water. The organic phases are combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. The residue gives 1.95 g (55%) of 3-(4-ethoxyphenyl)-5-pivaloyloxybenzofuran-2-one, oil (compound (135), Table 1).

Workup

temperatureThe clear, homogeneous reaction mixture is then refluxed for 2.5 hours
concentrationconcentrated under a slight vacuum
washwashed with saturated sodium bicarbonate solution and water
dry with materialdried over sodium sulfate
concentrationconcentrated on a vacuum rotary evaporator

Sources & evidence

ORD record: ord-f11057f217d245a48009c30b41a1dd82
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05367008

Reaction notes

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