Tetrabutylammonium Hydroxide → 2-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl-methoxy-ethoxy)-benzoic acid

HRID 512924Notes

Reaction equation

HRID 512924 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C:12]([O:35][CH3:36])([C:16]1[CH:21]=[CH:20][CH:19]=[C:18](/[CH:22]=[CH:23]/[C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][C:28]([Cl:34])=[CH:29][CH:30]=3)[N:25]=2)[CH:17]=1)[CH:13]1[CH2:15][CH2:14]1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:34][C:28]1[CH:27]=[C:26]2[C:31]([CH:32]=[CH:33][C:24](/[CH:23]=[CH:22]/[C:18]3[CH:17]=[C:16]([C:12]([O:35][CH3:36])([CH:13]4[CH2:15][CH2:14]4)[CH2:11][O:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([OH:37])=[O:2])[CH:21]=[CH:20][CH:19]=3)=[N:25]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 1317332782-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl-methoxy-ethoxy)-benzoic acid methyl ester

Product 1

HCID 1317332792-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl-methoxy-ethoxy)-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of ester 45 (1.0 g, 0.0019 mol) in THF (10.0 ml) was treated with a 20% aqueous solution of tetra-n-butylammonium hydroxide (2.5 ml), at ambient temperature for 15 hours. The solvents were evaporated, the resulting mixture was diluted with aqueous acetic acid and extracted with dichloromethane (30 ml) followed by usual workup and FC to give (Ia.96) (0.8 g, 79%).

Workup

  1. customThe solvents were evaporated
  2. additionthe resulting mixture was diluted with aqueous acetic acid
  3. extractionextracted with dichloromethane (30 ml)
  4. customto give (Ia.96) (0.8 g, 79%)

Sources & evidence

ORD record
ord-01b8246dd60c40d39baff2a612f3ae1b
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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