Tetrahydrofuran → 3,5-Dihydroxy-1-adamantyl methacrylate

HRID 1936524Notes

Reaction equation

HRID 1936524 reaction equation
[C:1]12([OH:13])[CH2:10][C:5]3([OH:11])[CH2:6][CH:7]([CH2:9][C:3]([OH:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.O1CCCC1.[C:26](Cl)(=[O:30])[C:27]([CH3:29])=[CH2:28]>O>[C:26]([O:13][C:1]12[CH2:10][C:5]3([OH:11])[CH2:6][CH:7]([CH2:9][C:3]([OH:12])([CH2:4]3)[CH2:2]1)[CH2:8]2)(=[O:30])[C:27]([CH3:29])=[CH2:28]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 98990221,3,5-Adamantanetriol

Product 1

HCID 130073943,5-Dihydroxy-1-adamantyl methacrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 mmol of 1,3,5-adamantanetriol, 10 mmol of triethylamine, and 40 ml of tetrahydrofuran were mixed, and 10 mmol of methacrylic acid chloride was added dropwise to the mixture for about 30 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 24 hours. After the reaction had been completed, to the reaction mixture was added water, followed by purification by column chromatography to give 1-methacryloyloxy-3,5-dihydroxyadamantane.

Workup

  1. additionAfter completion of the dropwise addition
  2. customfollowed by purification by column chromatography

Sources & evidence

ORD record
ord-117c406f89914498bb4879bfd9ee1c9f
Source dataset
uspto-grants-2002_05
Patent number
US06391520B1

Reaction notes

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