Hydrochloric Acid → HCID 69155937, compound

HRID 1836919Notes

Reaction equation

HRID 1836919 reaction equation
C[C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]3[C:29]([CH2:30][N:31]4[CH:35]=[CH:34][CH:33]=[N:32]4)=[CH:28][C:27]4[C:26]([CH3:37])([CH3:36])[CH2:25][CH2:24][C:23]([CH3:39])([CH3:38])[C:22]=4[CH:21]=3)=[CH:14][CH:13]=2)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O-:7])=[O:6].Cl>[Li+].[OH-].C(O)C>[CH3:36][C:26]1([CH3:37])[CH2:25][CH2:24][C:23]([CH3:38])([CH3:39])[C:22]2[CH:21]=[C:20]([CH2:19][CH2:18][C:15]3[CH:16]=[CH:17][C:12]([O:11][C:3]4[CH:2]=[CH:10][CH:9]=[CH:8][C:4]=4[C:5]([OH:7])=[O:6])=[CH:13][CH:14]=3)[C:29]([CH2:30][N:31]3[CH:35]=[CH:34][CH:33]=[N:32]3)=[CH:28][C:27]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86585398HCID 86585398, compound

Product 1

HCID 69155937HCID 69155937, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3939Lithium HydroxideSolvent

Procedure

A solution of 0.131 g (0.293 mmol) of Methyl-4-[2-(5,5,8,8-tetramethyl-3-(pyrazol-1-ylmethyl)-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl]phenoxybenzoate in 3 ml 1M LiOH and 10 ml ethyl alcohol was heated to reflux. After 2 hours the reaction was cooled to room temperature and acidified with 1M hydrochloric acid. The aqueous layer was extracted with ethyl ether, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography (gradient elution with 10% methanol/dichloromethane-10% methanol/dichloromethane with 5% acetic acid) to afford 0.101 g (79%) of 4-[2-(5,5,8,8-tetramethyl-3-((pyrazol-1-yl)methyl)-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl]phenoxy benzoic acid (M+1=433).

Workup

  1. extractionThe aqueous layer was extracted with ethyl ether
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (gradient elution with 10% methanol/dichloromethane-10% methanol/dichloromethane with 5% acetic acid)

Sources & evidence

ORD record
ord-71b34cfd173f4ef2b37a3f1e5fe3439a
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

Loading…