Water → HCID 66652135, compound

HRID 418929Notes

Reaction equation

HRID 418929 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH2:7][CH:8]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:9]3[CH2:19][CH2:18][CH2:17][CH:10]3[C:11]=2[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:16][O:15][C:13]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH:9]3[CH2:19][CH2:18][CH2:17][CH:10]32)=[C:5]([CH2:3][OH:2])[CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66652671HCID 66652671, compound

Product 1

HCID 66652135HCID 66652135, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 8-Methoxy-4-(4-methoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalene-6-carboxylic acid methyl ester (0.16 g, 0.44 mmol), lithium aluminum hydride (0.08 g, 1.31 mmol) in tetrahydrofuran (10 ml) and stir for 2.5 hours. Add water (0.05 g), add 15% NaOH (0.05 g), add water (0.15 g) and stir 30 minutes. Add EtOAC, filter ppt. Rinse organic layer with water, then 1 n HCl, then water. Dry over anhydrous sodium sulfate and remove solvent in vacuo to yield the titled compound (0.153 g, 100%). H NMR (CDCl3): 7.22 (d, J=8.8, Hz, 2H), 6.87 (d, J=8.4 Hz, 2H), 6.82 (s, 1H), 6.71(s, 1H), 4.7 (s, 2H), 3.81 (s, 3H), 3.45 (m, 1H), 3.1 (m, 1H), 2.85 (m, 2H), 2.55 (m, 1H), 2.2 (m, 1H), 1.6-1.3 (m, 5H).

Workup

  1. filtrationAdd EtOAC, filter ppt
  2. dry with materialDry over anhydrous sodium sulfate
  3. customremove solvent in vacuo

Sources & evidence

ORD record
ord-e8fdc0d55e9b439580c977b203eb4621
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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