Lithium hydroxide, monohydrate → (E)-[2-Methyl-4-[3(2-methylbenzo[b]furan-5-yl)-3-[4-(3-(morpholin-4-yl)propynyl)phenyl]-allyloxy]phenoxy]acetic acid

HRID 1039470Notes

Reaction equation

HRID 1039470 reaction equation
[CH3:1][C:2]1[CH:13]=[C:12]([O:14][CH2:15]/[CH:16]=[C:17](/[C:33]2[CH:42]=[CH:41][C:36]3[O:37][C:38]([CH3:40])=[CH:39][C:35]=3[CH:34]=2)\[C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:20][CH:19]=2)[CH:11]=[CH:10][C:3]=1[O:4][CH2:5][C:6]([O:8]C)=[O:7].O.[OH-].[Li+]>C(O)C.O>[CH3:1][C:2]1[CH:13]=[C:12]([O:14][CH2:15]/[CH:16]=[C:17](/[C:33]2[CH:42]=[CH:41][C:36]3[O:37][C:38]([CH3:40])=[CH:39][C:35]=3[CH:34]=2)\[C:18]2[CH:19]=[CH:20][C:21]([C:24]#[C:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:22][CH:23]=2)[CH:11]=[CH:10][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86629295methyl (E)-[2-methyl-4-[3-(2-methyl benzo[b]furan-5-yl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]-allyloxy]phenoxy]acetate

Product 1

HCID 23633996(E)-[2-Methyl-4-[3(2-methylbenzo[b]furan-5-yl)-3-[4-(3-(morpholin-4-yl)propynyl)phenyl]-allyloxy]phenoxy]acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The above ester (0.34 g, 0.60 mmol) was dissolved in ethanol (30 mL), a solution of lithium hydroxide monohydrate (0.08 g, 1.9 mmol) in water (3 mL) was added and the mixture was left to stand for 48 h. The solvents were evaporated in vacuo; the residue was diluted with water (25 mL) and acidified with acetic acid (0.3 mL). The formed precipitate was filtered off and dried in the air yielding the title compound as amorphous solid.

Workup

  1. waitthe mixture was left
  2. customThe solvents were evaporated in vacuo
  3. additionthe residue was diluted with water (25 mL)
  4. filtrationThe formed precipitate was filtered off
  5. customdried in the air

Sources & evidence

ORD record
ord-5331068cec9e49d78375aec3371cbb90
Source dataset
uspto-grants-2013_10
Patent number
US08551993B2

Reaction notes

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