Diisopropylamine → Methyl 2-methoxy-3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propanoate

HRID 620555Notes

Reaction equation

HRID 620555 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].[C:20]1([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=2[CH:36]=[O:37])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH3:13][O:14][CH:15]([CH:36]([OH:37])[C:35]1[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 80507Methyl methoxyacetateHCID 98176132-(8-Phenyloctyl)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 15617503Methyl 2-methoxy-3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To tetrahydrofuran (50 ml), cooled to -78° C. under argon, was added diisopropylamine (5.7 ml, 0.041 mole) followed by n-butyllithium (16 ml, 0.041 mole) slowly. After 15 minutes, methyl methoxyacetate (4.25 g, 0.041 mole) in tetrahydrofuran (10 ml) was added dropwise. The resulting solution was stirred for 30 minutes after which a solution of 2-(8-phenyloctyl)benzaldehyde in tetrahydrofuran (10 ml) was added dropwise. After 2 hours the reaction mixture was quenched with a solution of saturated ammonium chloride and then diluted with ice water. The aqueous layer was extracted with ether. The combined ether extract was washed with 10% sodium hydroxide (ice cold), dried over magnesium sulfate, filtered and evaporated to give the desired product.

Workup

  1. additionwas added dropwise
  2. customAfter 2 hours the reaction mixture was quenched with a solution of saturated ammonium chloride
  3. additiondiluted with ice water
  4. extractionThe aqueous layer was extracted with ether
  5. extractionThe combined ether extract
  6. washwas washed with 10% sodium hydroxide (ice cold)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-0724cb3f0f4846d9b77d89be54ee01c4
Source dataset
uspto-grants-1989_04
Patent number
US04820719

Reaction notes

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