Diisopropylamine → Methyl 2-methoxy-3-hydroxy-3-(2-dodecylphenyl)propionate

HRID 620554Notes

Reaction equation

HRID 620554 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].[CH2:20]([C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=[O:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1>[CH3:13][O:14][CH:15]([CH:34]([OH:35])[C:33]1[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 80507Methyl methoxyacetateHCID 140975722-DodecylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 15617501Methyl 2-methoxy-3-hydroxy-3-(2-dodecylphenyl)propionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of di-i-propylamine (0.77 ml, 5 mmoles) in tetrahydrofuran (10 ml) at -78° C. was added n-butyl lithium (2.1 ml, 5.5 mmoles) under argon atmosphere. After 15 minutes, methyl methoxyacetate (0.52 g, 5 mmoles) in tetrahydrofuran (2 ml) was added dropwise, with stirring. The resulting enolate solution was stirrred at -78° C. for 45 minutes. A solution of 2-dodecylbenzaldehyde (1.65 g, 6 mmoles) in tetrahydrofuran (2 ml) was added. The resulting light-blue mixture became a suspension after 1.5 hours. The reaction mixture was quenched with saturated ammonium chloride solution, diluted with ether and ice-water. The aqueous phase was extracted with ether. The combined organic extract was washed with saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to give the product, which was purified by flash column chromatography (silica, 15% ethyl acetate/hexane). The fractions were pooled to give 620 mg (33%).

Workup

  1. customafter 1.5 hours
  2. customThe reaction mixture was quenched with saturated ammonium chloride solution
  3. additiondiluted with ether and ice-water
  4. extractionThe aqueous phase was extracted with ether
  5. extractionThe combined organic extract
  6. washwas washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto give the product, which
  10. customwas purified by flash column chromatography (silica, 15% ethyl acetate/hexane)
  11. customto give 620 mg (33%)

Sources & evidence

ORD record
ord-81a49fc5dedd4529b81c8e25fcbb9cf7
Source dataset
uspto-grants-1989_04
Patent number
US04820719

Reaction notes

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