2-Hydroxyethyl acrylate → 1-Acryloyloxyethoxycarbonyl-3,5,7-adamantanetriol

HRID 1936527Notes

Reaction equation

HRID 1936527 reaction equation
[C:1]([C:4]12[CH2:14][C:8]3([OH:15])[CH2:9][C:10]([OH:13])([CH2:12][C:6]([OH:16])([CH2:7]3)[CH2:5]1)[CH2:11]2)([OH:3])=[O:2].[C:17]([O:21][CH2:22][CH2:23]O)(=[O:20])[CH:18]=[CH2:19]>C1(C)C=CC=CC=1>[C:17]([O:21][CH:22]([O:2][C:1]([C:4]12[CH2:5][C:6]3([OH:16])[CH2:7][C:8]([OH:15])([CH2:9][C:10]([OH:13])([CH2:12]3)[CH2:11]1)[CH2:14]2)=[O:3])[CH3:23])(=[O:20])[CH:18]=[CH2:19]

Participants

4

Reactant 2

HCID 131652-Hydroxyethyl acrylateHCID 120393761-Carboxy-3,5,7-trihydroxyadamantane

Product 1

HCID 224620081-Acryloyloxyethoxycarbonyl-3,5,7-adamantanetriol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 mmol of 1-carboxy-3,5,7-adamantanetriol and 2.5 mmol of 2-hydroxyethyl acrylate were reacted in toluene to give 1-acryloyloxyethoxycarbonyl-3,5,7-adamantanetriol. To 30 ml of tetrahydrofuran were added 5 mmol of 1-acryloyloxyethoxycarbonyl-3,5,7-adamantanetriol, 25 mmol of acetoaldehyde, and 1 mmol of p-toluenesulfonic acid, and the mixture was acetalized in the same manner as in Example 1 to give the object compound 1-acryloyloxyethoxycarbonyl-3,5,7-tri(1-hydroxyethoxy)adamantane (actalilzed compound) shown by the following formula.

Sources & evidence

ORD record
ord-431e78e2c78345008b904dd111ed5ef8
Source dataset
uspto-grants-2002_05
Patent number
US06391520B1

Reaction notes

Loading…