Water → HCID 22630261, compound

HRID 2416357Notes

Reaction equation

HRID 2416357 reaction equation
[CH2:1]([O:6][C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([F:29])[CH:23]=4)=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:30](O)(=[O:33])[CH:31]=[CH2:32].Cl.C(N=C=NCCCN(C)C)C.O>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([O:6][C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][C:30](=[O:33])[CH:31]=[CH2:32])=[C:24]([F:29])[CH:23]=4)=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 962WaterHCID 6581Acrylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22630264HCID 22630264, compound

Product 1

HCID 22630261HCID 22630261, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

2-Pentyloxy-7-(2-(3-fluoro-4-hydroxyphenyl)ethyl)fluorene (0.7 g) and acrylic acid (0.14 g) were dissolved in chloroform (30 mL) and cooled down to 0° C. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.44 g) and 4-dimethylaminopyridine (0.01 g) were added thereto, and then the temperature was allowed to come back to a room temperature, followed by stirring for 24 hours. Water was added to separate the solution, and the chloroform layer was dried on anhydrous magnesium sulfate. A residue obtained by distilling chloroform off was purified by means of column chromatography (silica gel, eluting solvent: toluene), and it was further recrystallized to obtain 2-pentyloxy-7-(2-(3-fluoro-4-acryloyloxyphenyl)ethyl)fluorene (0.14 g) of the intended product.

Workup

  1. customto come back to a room temperature
  2. customto separate the solution
  3. dry with materialthe chloroform layer was dried on anhydrous magnesium sulfate
  4. customA residue obtained
  5. distillationby distilling chloroform
  6. customoff was purified by means of column chromatography (silica gel, eluting solvent: toluene), and it
  7. customwas further recrystallized

Sources & evidence

ORD record
ord-fb8467405c79497dae520dc13fc940e3
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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