1-Acetoxy-2-bromoethane → Pivalic acid 6-[2-(ethoxycarbonylmethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-yl ester

HRID 1950640Notes

Reaction equation

HRID 1950640 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:14]=[CH:13][C:12]=2[CH2:11]1.[C:27]([O:30][CH2:31][CH2:32]Br)(=[O:29])[CH3:28].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:31]([O:30][C:27]([CH2:28][NH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([O:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:25])[CH3:24])[CH:14]=[CH:13][C:12]=2[CH2:11]1)=[O:29])[CH3:32]

Participants

6

Reactant 4

HCID 135641-Acetoxy-2-bromoethaneHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 66626486Pivalic acid 6-(2-amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57933970Pivalic acid 6-[2-(ethoxycarbonylmethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-yl esterYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of pivalic acid 6-(2-amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (110 mg), bromoethyl acetate (400 mg), sodium acetate (200 mg) and ethanol (2 ml) was refluxed overnight. A saturated aqueous solution of sodium bicarbonate was added, and the solution was extracted with ethyl acetate. The solution was washed with brine, dried over magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (83 mg).

Workup

  1. temperaturewas refluxed overnight
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-3afdcd2ec72e4f809443bc75cc1e530c
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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