Tetrahydrofuran → 3-Hydroxy-1-adamantyl acrylate

HRID 2305279Notes

Reaction equation

HRID 2305279 reaction equation
[C:1]12([OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.[O:20]1C[CH2:23][CH2:22][CH2:21]1.C(Cl)(=O)C=C>O>[C:21]([O:12][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2)(=[O:20])[CH:22]=[CH2:23]

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

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

Workup

  1. additionwas added drop wise over about 30 minutes
  2. additionAfter the completion of addition
  3. extractionthe mixture was then extracted with ethyl acetate
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-a07c6af3a1084cefaec52e1ba2f69a90
Source dataset
uspto-grants-2002_08
Patent number
US06440636B1

Reaction notes

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