Tetrahydrofuran → 3-Hydroxy-1-adamantyl acrylate

HRID 2120522Notes

Reaction equation

HRID 2120522 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]12([OH:17])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([OH:16])([CH2:9]3)[CH2:7]1)[CH2:13]2.C(N(CC)CC)C.O1CCCC1>O>[C:1]([O:17][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([OH:16])([CH2:9]3)[CH2:7]1)[CH2:13]2)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 5738291,3-Adamantanediol

Product 1

HCID 222287903-Hydroxy-1-adamantyl acrylateYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A total of 13 mmole of acrylyl chloride was added dropwise to a mixture of 10 mmole of 1,3-adamantanediol, 15 mmole of triethylamine and 100 ml of tetrahydrofuran over about 30 minutes. After the completion of addition, the resulting mixture was stirred at 50° C. for 1.5 hours. After adding water, the reaction mixture was extracted with ethyl acetate, the organic layer was concentrated, and the resulting concentrate was subjected to column chromatography on a silica gel to thereby yield the title compound in a yield of 63%.

Workup

  1. additionAfter the completion of addition
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. concentrationthe organic layer was concentrated
  4. concentrationthe resulting concentrate

Sources & evidence

ORD record
ord-7a4567ec83f94880a6e9893fef2df90a
Source dataset
uspto-grants-2004_02
Patent number
US06692889B1

Reaction notes

Loading…