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Triethylamine → 2-Dimethylaminopyridine

HRID 478979
Notes
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Reaction equation

HRID 478979 reaction equation
CC1(O)C2CC3CC(CC1C3)C2.C(OC(=O)C(C)=C)(=O)C(C)=C.[CH2:24]([N:26](CC)[CH2:27]C)C.C[C:32]1(C)[N:37]([O])[C:36](C)(C)[CH2:35][CH2:34][CH2:33]1>C1(C)C=CC=CC=1>[CH3:24][N:26]([C:36]1[CH:35]=[CH:34][CH:33]=[CH:32][N:37]=1)[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12974Methacrylic anhydrideHCID 1365452-Methyl-2-adamantanolHCID 2724126Tempo

Product 1

HCID 218852-DimethylaminopyridineYield 40%

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent

Procedure

A glass flask equipped with a stirrer, two dropping funnels, a thermometer and a Dimroth condenser was charged with 16.6 g (0.1 mol) of 2-methyl-2-adamantanol, 23.1 g (0.15 mol) of methacrylic anhydride of 97% purity which is obtained by the process of example 1, 15.7 g (0.155 mol) of triethylamine, 0.6 g (0.005 mol) of dimethylaminopyridine, 70 ml of toluene and 0.005 g of HO-TEMPO, and the mixture was heated and stirred at 50° C. for 31 hours. It was confirmed that 2-methyl-2-adamantyl methacrylate was formed in the reaction mixture in a yield of about 40%. The resultant 2-methyl-2-adamantyl methacrylate was chromatographed on silica gel to obtain 9.1 g of 2-methyl-2-adamantyl methacrylate.

Workup

  1. customA glass flask equipped with a stirrer

Sources & evidence

ORD record
ord-659aad3e821c46a8bb7a614ad8a38e1e
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06642394B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes