Sodium Hydroxide → HCID 57871397, compound

HRID 550219Notes

Reaction equation

HRID 550219 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:34])[CH:21]=3)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[OH-].[Na+]>C1COCC1.CO>[CH3:32][C:29]([CH3:30])([CH3:31])[C:28](=[O:33])[CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:15]([C:9]2[CH:8]=[C:7]3[C:12]([CH:13]=[CH:14][C:5]([C:3]([OH:4])=[O:2])=[CH:6]3)=[CH:11][CH:10]=2)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:21][C:22]=1[CH3:34]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57871409HCID 57871409, compound

Product 1

HCID 57871397HCID 57871397, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Treat 7-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carboxylic acid methyl ester (1.1 g, 2.4 mmol) in THF (15 mL) and MeOH (30 mL) with 2N NaOH (6.0 mL, 12.0 mmol) and heat to 55° C. for 16 h. Then concentrate the reaction mixture and dilute the residue with CH2CL2 and water (50 mL each). Acidify the mixture to pH 1 using 1N HCl. Discard the aqueous layer and wash the organic layer with brine. Dry the organic layer over Na2SO4, filter and concentrate the filtrate. Purify by silica gel radial chromatography (2:98 MeOH:CH2CL2 to 10:90 MeOH:CH2CL2) to give the title compound as a yellow solid (0.96 g, 90%). MS (ES) m/e 447 (M+1).

Workup

  1. concentrationThen concentrate the reaction mixture
  2. additiondilute the residue with CH2CL2 and water (50 mL each)
  3. washwash the organic layer with brine
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate the filtrate
  7. customPurify by silica gel radial chromatography (2:98 MeOH:CH2CL2 to 10:90 MeOH:CH2CL2)

Sources & evidence

ORD record
ord-cc720c9afa5c4e99b2e85f9bedff417d
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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