Lithium hydroxide, monohydrate → (E)-3-(3'-Adamantan-1-yl-4'-cyanomethoxybiphenyl-4-yl)-acrylic acid

HRID 41728Notes

Reaction equation

HRID 41728 reaction equation
C[O:2][C:3](=[O:32])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]#[N:21])=[C:14]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:13]=2)=[CH:8][CH:7]=1.O[Li].O>C1COCC1.O>[C:22]12([C:14]3[CH:13]=[C:12]([C:9]4[CH:8]=[CH:7][C:6](/[CH:5]=[CH:4]/[C:3]([OH:32])=[O:2])=[CH:11][CH:10]=4)[CH:17]=[CH:16][C:15]=3[O:18][CH2:19][C:20]#[N:21])[CH2:23][CH:24]3[CH2:25][CH:26]([CH2:27][CH:28]([CH2:30]3)[CH2:29]1)[CH2:31]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67399554(E)-3-(3'-adamantan-1-yl-4'-cyanomethoxybiphenyl-4-yl)-acrylic acid methyl ester

Product 1

HCID 46830625(E)-3-(3'-Adamantan-1-yl-4'-cyanomethoxybiphenyl-4-yl)-acrylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

(E)-3-(3′-Adamantan-1-yl-4′-cyanomethoxybiphenyl-4-yl)-acrylic acid methyl ester (240 mg, 0.56 mmol) was added to a solution of LiOH.H2O (117 mg, 2.8 mmol) in 24 ml of THF:H2O 1:1. The solution thus obtained was kept under stirring at RT overnight. THF was removed under reduced pressure and the resulting aqueous layer acidified with 1N HCl to allow the formation of the title compound as a white precipitate that was filtered (216 mg, 93%).

Workup

  1. customThe solution thus obtained
  2. customTHF was removed under reduced pressure
  3. filtrationwas filtered (216 mg, 93%)

Sources & evidence

ORD record
ord-bb5cc6a1eb00479a8f1f3673fb64a002
Source dataset
uspto-grants-2013_09
Patent number
US08530517B2

Reaction notes

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