Water → HCID 22106652, compound

HRID 482366Notes

Reaction equation

HRID 482366 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:43])([CH3:42])[CH:5]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]=2)=[CH:26][CH:25]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:42][C:4]([CH3:43])([CH:5]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]=2)=[CH:26][CH:25]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:8][CH:7]=1)[CH2:3][OH:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10722005HCID 10722005, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22106652HCID 22106652, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution in THF (50 mL) at ambient temperature of 2,2-dimethyl-3,3-bis(4-(2-quinolylmethoxy)phenyl)propionic acid methyl ester (1.33 g, 2.28 mmole), prepared as in Example 26, step 2, was added LiAlH4 (0.09 g, 2.5 mmol) in a single portion. The mixture was stirred 3 hours at ambient temperature. Water (0.1 mL) was added followed by aqueous 1N NaOH (0.1 ml) and water (0.5 mL). The mixture was then concentrated to dryness and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (60% ethylacetate/hexanes) gave 1.01 g (80%) of 2,2-dimethyl-3,3-bis(4-(2-quinolylmethoxy)phenyl)-propan-1-ol as a yellow foam.

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel (60% ethylacetate/hexanes)

Sources & evidence

ORD record
ord-2a7e74c94eda4b7d9c523baf0e46d8ac
Source dataset
uspto-grants-1998_08
Patent number
US05795900

Reaction notes

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