Pyridine → 4-(4-Dimethylaminophenylcarbonyloxymethyl)-2,2-dimethyl-1,3-dioxolane

HRID 251519Notes

Reaction equation

[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[OH:13][CH2:14][CH:15]1[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]1.N1C=CC=CC=1>O>[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:13][CH2:14][CH:15]2[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]2)=[O:8])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 85 °C

Procedure

4-Dimethylaminobenzoyl chloride (1.00 g, 5 mmol) is added in one portion to a mixture of 4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (1.19 g, 10 mmol) and abs. pyridine (20 ml), and the mixture is stirred at room temperature for 10 min. The mixture is subsequently stirred at 80-90° C. for 2 h. Water (50 ml) is added, the reaction mixture is extracted with dichloromethane (3×25 ml), and the combined organic extracts are dried over magnesium sulfate. The solvent is removed in vacuo, and the residue is purified by column chromatography.

Workup

extractionthe reaction mixture is extracted with dichloromethane (3×25 ml)
dry with materialthe combined organic extracts are dried over magnesium sulfate
customThe solvent is removed in vacuo
customthe residue is purified by column chromatography

Sources & evidence

ORD record: ord-0b0f1df809d2494183511b4d523a4659
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863478B2

Reaction notes

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