Tetrahydrofuran → 3-Hydroxy-1-adamantyl acrylate

HRID 1267551Notes

Reaction equation

HRID 1267551 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 acryloyl 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 the addition of 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-d2f7737bec514fc29c95954b237ede3c
Source dataset
uspto-grants-2003_04
Patent number
US06552143B2

Reaction notes

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