Tetrahydrofuran → HCID 86676424, compound

HRID 1810725Notes

Reaction equation

C1COCC1.[CH3:6][O:7][C:8]1[CH:23]=[CH:22][C:11]([CH:12]([OH:21])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.[C:24](Cl)(=[O:28])[C:25]([CH3:27])=[CH2:26]>N1C=CC=CC=1>[C:24]([O:21][CH:12]([C:11]1[CH:22]=[CH:23][C:8]([O:7][CH3:6])=[CH:9][CH:10]=1)[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)(=[O:28])[C:25]([CH3:27])=[CH2:26]

Participants

Conditions

Temperature: -10 °C

Procedure

In a 1 L round-bottom flask equipped with magnetic stirrer and nitrogen inlet was added 700 ml anhydrous THF containing BHT as inhibitor, 98 g anhydrous pyridine, and 51.6 g (211 mmol) of 4,4′-dimethoxybenzhydrol. The reaction mixture was cooled to −10° C. and 26.5 g (254 mmol) methacryloyl chloride was added dropwise over 10 minutes. The reaction mixture was stirred at −10-0° C. for 1 hour and then stirred at ambient temperature for 20 hours. The solid was filtered and the filtrate was extracted using Et2O/water. The organic layer was washed with 1 N NaHCO3, 1 N HCl, brine, and water and then dried with MgSO4, filtered, and concentrated under reduced pressure to give the desired crude product which was recrystallized from cold ether/hexanes at −20° C.

Workup

customIn a 1 L round-bottom flask equipped with magnetic stirrer and nitrogen inlet
stirringstirred at ambient temperature for 20 hours
filtrationThe solid was filtered
extractionthe filtrate was extracted
washThe organic layer was washed with 1 N NaHCO3, 1 N HCl, brine, and water
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0298e647975f4f908b963fa07f6e9b4f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362177B1

Reaction notes

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