Triethylamine → 2-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethyl methacrylate

HRID 886674Notes

Reaction equation

HRID 886674 reaction equation
[CH3:1][C:2]1([O:12][C:13](=[O:20])[CH2:14][O:15][C:16](=[O:19])[CH2:17][OH:18])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C(N(CC)CC)C.COC1C=CC(O)=CC=1.[C:37](Cl)(=[O:41])[C:38]([CH3:40])=[CH2:39]>C(OCC)C.C1COCC1>[C:37]([O:18][CH2:17][C:16]([O:15][CH2:14][C:13]([O:12][C:2]1([CH3:1])[CH:9]2[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]1[CH2:11]3)[CH2:10]2)=[O:20])=[O:19])(=[O:41])[C:38]([CH3:40])=[CH2:39]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 90154-MethoxyphenolHCID 13528Methacryloyl chlorideHCID 581059672-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethanol

Product 1

HCID 578287412-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethyl methacrylateYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2 liter 3-neck flask fitted with a thermometer, a cooling tube and a stirrer was charged with 165 g (584 mmol) of 2-(2-(2-methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethanol, 2,000 ml of THF, 105 ml (754 mmol) of triethylamine and 0.165 g (1,000 ppm) of p-methoxyphenol, and the mixture was stirred to form a solution. Following dissolution, the solution was cooled in an ice bath and 62.7 ml (648 mmol) of methacryloyl chloride was added gradually to the solution. The reaction mixture was then returned to room temperature, and stirred for 3 hours. Following completion of the reaction, 1,000 ml of diethyl ether was added, and the filtrate was washed 5 times with 200 ml samples of distilled water. The washed extract was then concentrated, yielding 198 g (yield: 97%, GC purity: 99%) of the targeted colorless liquid.

Workup

  1. customA 2 liter 3-neck flask fitted with a thermometer, a cooling tube and a stirrer
  2. customto form a solution
  3. dissolutiondissolution
  4. temperaturethe solution was cooled in an ice bath
  5. customwas then returned to room temperature
  6. stirringstirred for 3 hours
  7. additionwas added
  8. washthe filtrate was washed 5 times with 200 ml samples of distilled water
  9. extractionThe washed extract
  10. concentrationwas then concentrated
  11. customyielding 198 g (yield: 97%, GC purity: 99%) of the targeted colorless liquid

Sources & evidence

ORD record
ord-f0f95afe8bbd4af1abe71613e713a4bf
Source dataset
uspto-grants-2012_08
Patent number
US08247160B2

Reaction notes

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