Tetrahydrofuran → HCID 13007392, compound

HRID 1936522Notes

Reaction equation

HRID 1936522 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.[O:21]1C[CH2:24][CH2:23][CH2:22]1.C(Cl)(=O)C=C>O>[C:22]([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:21])[CH:23]=[CH2:24]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 98990221,3,5-Adamantanetriol

Product 1

HCID 13007392HCID 13007392, compound

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 acrylic acid chloride was added dropwise to this mixture for about 30 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 6 hours. After the reaction had been completed, to the reaction mixture was added water and the resultant mixture was purified by column chromatography to give 1-acryloyloxy-3,5-dihydroxyadamantane.

Workup

  1. additionAfter completion of the dropwise addition
  2. customthe resultant mixture was purified by column chromatography

Sources & evidence

ORD record
ord-65d433c9b89741ebb34e1c83877a514a
Source dataset
uspto-grants-2002_05
Patent number
US06391520B1

Reaction notes

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