Potassium Carbonate → Ethyl 4'-[5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentyloxy]-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

HRID 253512Notes

Reaction equation

HRID 253512 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[CH:20]=1.Br[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][N:39]1[C:43](=[O:44])[C:42]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:41]2[C:40]1=[O:49].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:49]=[C:40]1[C:41]2[C:42](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43](=[O:44])[N:39]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:31])([CH3:32])[C:21]=2[CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 136770N-(5-Bromopentyl)phthalimideHCID 57552328HCID 57552328, compound

Product 1

HCID 66856502Ethyl 4'-[5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentyloxy]-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylateYield 85.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a manner similar to that of Example 17a, by reaction of 600 mg (1.4 mmol) of ethyl 4′-hydroxy-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate with 500 mg (1.7 mmol) of N-(5-bromopentyl)phthalimide and 230 mg (1.66 mmol) of potassium carbonate in 50 ml of acetone. 770 mg of ethyl 4′-[5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentyloxy]-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a beige-colored solid (yield=85%).

Sources & evidence

ORD record
ord-7aace3f7ee76480089e85139b88fe47f
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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