Water → HCID 66856613, compound

HRID 253502Notes

Reaction equation

HRID 253502 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].C(=O)([O-])[O-].[K+].[K+].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:31][CH:30]=2)=[CH:25][C:24]=1[C:40]1[CH:49]=[CH:48][C:47]2[C:46]([CH3:51])([CH3:50])[CH2:45][CH2:44][C:43]([CH3:53])([CH3:52])[C:42]=2[CH:41]=1.O>CC(C)=O>[O:15]=[C:6]1[C:7]2[C:8](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:10])[N:5]1[CH2:4][CH2:3][CH2:2][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][CH:34]=2)=[CH:25][C:24]=1[C:40]1[CH:49]=[CH:48][C:47]2[C:46]([CH3:51])([CH3:50])[CH2:45][CH2:44][C:43]([CH3:52])([CH3:53])[C:42]=2[CH:41]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 57552328Ethyl 4'-hydroxy-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 66856613HCID 66856613, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

600 mg (2.24 mmol) of N-(3-bromopropyl)phthalimide and 310 mg (2.24 mmol) of potassium carbonate are added to a solution of 800 mg (1.86 mmol) of ethyl 4′-hydroxy-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate in 50 ml of acetone. The reaction mixture is stirred overnight at reflux. The reaction is stopped by adding water, and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off. The residue is precipitated from a small amount of ethyl acetate. It is filtered off and 700 mg of ethyl 4′-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propoxy]-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a white solid (yield=61%).

Workup

  1. temperatureat reflux
  2. extractionis then extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customThe residue is precipitated from a small amount of ethyl acetate
  6. filtrationIt is filtered off

Sources & evidence

ORD record
ord-08282139b6a54bb3899dcf97a3959c00
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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