Tetrahydrofuran → 1-(1-Acryloyloxy-1,2-dimethylpropyl)-3-hydroxyadamantane

HRID 2120528Notes

Reaction equation

HRID 2120528 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[OH:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][C:9]([C:17]([CH:20]([CH3:22])[CH3:21])([CH3:19])[OH:18])([CH2:10]3)[CH2:8]1)[CH2:14]2.C(N(CC)CC)C.O1CCCC1>O>[C:1]([O:18][C:17]([C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:16][C:7]([OH:6])([CH2:14]3)[CH2:8]1)[CH2:10]2)([CH3:19])[CH:20]([CH3:22])[CH3:21])(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 120106413-Hydroxy-alpha-isopropyl-alpha-methyl-1-adamantanemethanol

Product 1

HCID 226500711-(1-Acryloyloxy-1,2-dimethylpropyl)-3-hydroxyadamantaneYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A total of 10 mmole of acrylyl chloride was added dropwise to a mixture of 10 mmole of 3-hydroxy-α-isopropyl-α-methyl-1-adamantanemethanol thus obtained, 10 mmole of triethylamine and 40 ml of tetrahydrofuran over about 30 minutes. After the completion of addition, the resulting mixture was stirred at room temperature for 6 hours. After adding water, the reaction mixture was concentrated, and the concentrate was subjected to column chromatography on a silica gel to thereby yield the title compound in a yield of 67%.

Workup

  1. customthus obtained
  2. additionAfter the completion of addition
  3. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a22f1b920b344c1887f8e1e987bfe275
Source dataset
uspto-grants-2004_02
Patent number
US06692889B1

Reaction notes

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