Water → 8-(2-Furylmethoxy)-8-oxooctyl 2,5-bis[(4-{[6-(acryloyloxy)hexyl]oxy}benzoyl)oxy]benzoate

HRID 424313

Reaction equation

HRID 424313 reaction equation
Cl.CN(C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[OH:13][C:14]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][C:15]=1[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[O:31][CH:32]=[CH:33][CH:34]=1)=[O:27])=[O:17].C([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][O:50][C:51]1[CH:59]=[CH:58][C:54]([C:55]([OH:57])=O)=[CH:53][CH:52]=1)(=O)C=C.[OH2:60]>ClCCl.CN(C)C1C=CN=CC=1>[C:19]([O:18][CH2:16][CH2:15][CH2:14][CH2:38][CH2:37][CH2:36][O:39][C:4]1[CH:5]=[CH:6][C:34]([C:30]([O:13][C:14]2[CH:38]=[CH:37][C:36]([O:39][C:55](=[O:57])[C:54]3[CH:53]=[CH:52][C:51]([O:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][O:28][C:26](=[O:27])[CH:25]=[CH2:24])=[CH:59][CH:58]=3)=[CH:35][C:15]=2[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[O:27])=[O:17])=[O:31])=[CH:33][CH:32]=1)(=[O:60])[CH:20]=[CH2:21]

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22719187HCID 22719187, compoundHCID 590050178-(2-Furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate

Product 1

HCID 590050198-(2-Furylmethoxy)-8-oxooctyl 2,5-bis[(4-{[6-(acryloyloxy)hexyl]oxy}benzoyl)oxy]benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (4.8 g) in dichloromethane (60 ml) was slowly added to a solution of 8-(2-furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate (3.7 g), 4-(6-acryloylhexyloxy)benzoic acid (7.3 g) and 4-dimethylaminopyridine (0.6 g) in dichloromethane (150 ml) at 0° C. The mixture was stirred overnight at room temperature. The resulting solution was then added to water (600 ml) and extracted with dichloromethane (3×200 ml). The combined organic layers were washed with water (2×200 ml), dried over magnesium sulphate and filtered. The solvent removed in vacuum. The residue (10.4 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (95:5) as eluent, to give 8-(2-furylmethoxy)-8-oxooctyl 2,5-bis[(4-{[6-(acryloyloxy)hexyl]oxy}benzoyl)oxy]benzoate.

Workup

  1. extractionextracted with dichloromethane (3×200 ml)
  2. washThe combined organic layers were washed with water (2×200 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customThe solvent removed in vacuum
  6. customThe residue (10.4 g) was purified by column flash chromatography on silica gel

Sources & evidence

ORD record
ord-c05dcc7cef6c47b8acfdd0b6b67beead
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Linked notes

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