Water → HCID 68008604, compound

HRID 535155Notes

Reaction equation

HRID 535155 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1([CH2:20][C:21]2([CH2:34][CH2:35][C:36](OCC)=[O:37])[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[OH:3][CH2:4][CH2:5][CH2:6][C:7]1([CH2:20][C:21]2([CH2:34][CH2:35][CH2:36][OH:37])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:28]3[C:33]2=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68008589HCID 68008589, compound

Product 1

HCID 68008604HCID 68008604, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{9-[9-(2-Ethoxycarbonylethyl)-9H-fluoren-9-ylmethyl]-9H-fluoren-9-yl}-propionic acid ethyl ester (9.7 g) was dissolved in 200 mL of THF and treated with lithium aluminum hydride (1.97 g) at 0° C. under an atmosphere of nitrogen. After stirring overnight, the reaction mixture was treated with 2.0 mL of water followed by 2.0 mL of 15% NaOH solution and then 6.0 mL of water. The reaction mixture was filtered through a pad of CELITE, rinsing with ethyl acetate. The filtrate was washed with 1N HCl solution, water (2×) and brine. The organic portion was dried over Na2SO4, filtered, and concentrated under reduced pressure to give a white solid. The white solid was crystallized from toluene to give 5.85 g of the title compound as white crystals. 1H NMR (CDCl3, 500 MHz) δ 7.04 (m, 4H), 6.98 (m, 4H), 6.83-6.77 (m, 4H), 3.19 (t, J=6.4 Hz, 4H), 3.09 (s, 2H), 1.94 (m, 4H), 1.00 (br s, 2H), 0.47 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of CELITE
  2. washrinsing with ethyl acetate
  3. washThe filtrate was washed with 1N HCl solution, water (2×) and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a white solid
  8. customThe white solid was crystallized from toluene

Sources & evidence

ORD record
ord-c47327b4f3f847d3b25bf8aa100bb127
Source dataset
uspto-grants-2014_10
Patent number
US08854730B2

Reaction notes

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