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

HRID 909976Notes

Reaction equation

HRID 909976 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.C1COCC1.C(N(CC)CC)C.[C:33](Cl)(=[O:37])[C:34]([CH3:36])=[CH2:35]>COC1C=CC(O)=CC=1.C(OCC)C>[C:33]([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:37])[C:34]([CH3:36])=[CH2:35]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 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 90154-MethoxyphenolCatalystHCID 3283Diethyl EtherSolvent

Procedure

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 were added to and dissolved in a 2 L three-neck flask equipped with a thermometer, a cooling pipe, and a stirring apparatus. After the dissolution, 62.7 mL (648 mmol) of methacryloyl chloride was gradually added thereto in an ice bath. Then, the resultant was heated at room temperature, and stirred for 3 hours. After the reaction, 1,000 mL of diethylether was added thereto, and then washed 5 times using 200 mL of distilled water. The extraction liquid was concentrated, thereby obtaining 198 g of the intended compound in the form of a colorless liquid (yield: 97%, GC purity: 99%).

Workup

  1. dissolutiondissolved in a 2 L three-neck flask
  2. customequipped with a thermometer
  3. additionwas gradually added
  4. additionwas added
  5. washwashed 5 times
  6. extractionThe extraction liquid
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-0c22fb64994b4963b3c3aaa28a14adde
Source dataset
uspto-grants-2011_09
Patent number
US08021823B2

Reaction notes

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