Lithium Hydroxide → HCID 86585391, compound

HRID 1836912Notes

Reaction equation

HRID 1836912 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[C:21]([CH2:22][N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)=[CH:20][C:19]3[C:18]([CH3:29])([CH3:28])[C@@H:17]([O:30]C(=O)C)[C@@H:16]([O:34]C(=O)C)[C:15]([CH3:39])([CH3:38])[C:14]=3[CH:13]=2)=[CH:6][CH:5]=1.[Li+].[OH-]>CO>[CH3:28][C:18]1([CH3:29])[C@@H:17]([OH:30])[C@@H:16]([OH:34])[C:15]([CH3:38])([CH3:39])[C:14]2[CH:13]=[C:12](/[CH:11]=[CH:10]/[C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:40])=[O:2])=[CH:5][CH:6]=3)[C:21]([CH2:22][N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)=[CH:20][C:19]1=2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86585392HCID 86585392, compound

Product 1

HCID 86585391HCID 86585391, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.0 g (2.2 mmol) of 4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6,7-cis-diacetoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoic acid methyl ester. in 20 ml of methyl alcohol and 10 ml of 1 N LiOH was heated at reflux. After 1 h, cooled to room temperature, concentrated under reduced pressure, acidified with 2 N HCl, extracted with ethyl acetate, washed with brine, dried over sodium sulfate and adsorbed onto silica gel. The product was purified by flash chromatography (gradient elution: 20-60% ethyl acetate/hexane with 0.2% acetic acid) to give 560 mg of 4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6,7-cis-dihydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid.(mp 238.3-241.5) 148.

Workup

  1. temperatureat reflux
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe product was purified by flash chromatography (gradient elution: 20-60% ethyl acetate/hexane with 0.2% acetic acid)

Sources & evidence

ORD record
ord-8f2ecfab66174c869b6373992fadaaf9
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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