Triethylamine → HCID 3239817, compound

HRID 1019286Notes

Reaction equation

HRID 1019286 reaction equation
[OH:1][C:2]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:4]([O:5][C:6]3=[O:13])[CH2:3]1)[CH2:10]2.[C:14](Cl)(=[O:17])[CH:15]=[CH2:16].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:14]([O:1][C:2]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:4]([O:5][C:6]3=[O:13])[CH2:3]1)[CH2:10]2)(=[O:17])[CH:15]=[CH2:16].[OH:1][C:2]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:4]([O:5][C:6]3=[O:13])[CH2:3]1)[CH2:10]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 3239817HCID 3239817, compound

Product 2

HCID 3239817HCID 3239817, compoundHCID 9859508HCID 9859508, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 50 mmol of 1-hydroxy-4-oxatricyclo[4.3.1.13,8]undecan-5-one, 150 mmol of acryloyl chloride, 150 mmol of triethylamine, and 250 ml of toluene was stirred at 60° C. for 4 hours. The resulting reaction mixture was concentrated and was then subjected to column chromatography on a silica gel to yield 1-acryloyloxy-4-oxatricyclo[4.3.1.13,8]undecan-5-one of the following formula in a yield of 50% with a conversion rate from 1-hydroxy-4-oxatricyclo[4.3.1.13,8]undecan-5-one of 73%.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-256132eb076b432cb78978f90e1ef8e3
Source dataset
uspto-grants-2002_11
Patent number
US06486330B1

Reaction notes

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