Lithium Hydroxide → HCID 10698648, compound

HRID 1456865Notes

Reaction equation

HRID 1456865 reaction equation
C1COCC1.C[O:7][C:8](=[O:49])[C:9]([CH3:48])([CH3:47])[CH:10]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=2)=[CH:31][CH:30]=1)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:13][CH:12]=1.O[Li].O.[Li+].[OH-]>CO>[CH3:47][C:9]([CH3:48])([CH:10]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=2)=[CH:31][CH:30]=1)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:13][CH:12]=1)[C:8]([OH:49])=[O:7]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 10722005HCID 10722005, compound

Product 1

HCID 10698648HCID 10698648, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution in methanol (8 mL) and THF (4 mL) of 2,2-dimethyl-3,3-bis(4-(2-quinolylmethoxy)phenyl)propionic acid methyl ester (0.4 g, 0.69 mmol), prepared as in step 2, was added LiOH.H2O (4 ml, 4 mmole, 1M solution) dropwise, and the mixture was stirred overnight after which an additional 2 mL of the LiOH solution was added and the mixture was stirred an additional 24 hours. The mixture was concentrated to dryness, acidified with excess 0.5M citric acid, diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (7% MeOH/CH2Cl2) provided 0.16 g (40%) of 2,2-dimethyl-3,3-bis(4-(2-quinolylmethoxy)phenyl)propionic acid as a white solid: mp 124°-127° C. Anal. Calc'd. for C37H32 N2O4 : C, 78.14; H, 5.67; N 4.92. Found C, 77.45; H, 5.74; N, 4.67.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated to dryness
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography on silica gel (7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7cc9b208c1834fcd9e0e9e0f0e29e66d
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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