Water → HCID 10721188, compound

HRID 1456870Notes

Reaction equation

HRID 1456870 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:35]=2)=[CH:28][CH:27]=1)([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[CH:10][CH:9]=1)[CH3:7])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[N:35]=3)=[CH:28][CH:27]=2)([CH3:7])[CH2:5][CH2:4][OH:3])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10745843HCID 10745843, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10721188HCID 10721188, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution in THF (40 mL) of 3,3-bis(4-(2-quinolylmethoxy)phenyl)butanoic acid ethyl ester (3.2 g, 5.5 mmol), prepared as in Example 13, was added slowly a solution of LiAlH4 (1.0M, 6 mL, 6.0 mmol). The mixture was stirred for 2 hours and water (15 mL) was added slowly followed by aqueous 1N NaOH. The reaction mixture was diluted with THF (20 mL) and the mixture was filtered through a celite pad. The filtrate was extracted with ether and the organic extract was washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide 3,3-bis(4-(2-quinolylmethoxy)phenyl)butan-1-ol (2.4 g) as a pale yellow foam.

Workup

  1. filtrationthe mixture was filtered through a celite pad
  2. extractionThe filtrate was extracted with ether
  3. extractionthe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cd835be0b5e4f39a5b3cd19f61b8588
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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