Water → Methyl 2-[(2'-Methoxycarbonylbiphenyl-4-yl)methyl]-3-oxoheptanoate

HRID 865001Notes

Reaction equation

HRID 865001 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([O:30][CH3:31])=[O:29])=[CH:18][CH:17]=1.O>C1COCC1.C(O)(=O)C>[CH3:31][O:30][C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH:3]([C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5])=[CH:21][CH:20]=1)=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 546075Methyl 3-oxoheptanoateHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

Product 1

HCID 10738674Methyl 2-[(2'-Methoxycarbonylbiphenyl-4-yl)methyl]-3-oxoheptanoateYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Under nitrogen atmosphere, 2.3 of methyl 3-oxoheptanoate, dissolved into 10 ml of anhydrous THF were dropped into a suspension containing 0.22 g of 80% NaH in 30 ml g of anhydrous THF. After the effervescence was over, 2.22 g of 4-bromomethyl-2'-methoxycarbonylbiphenyl, dissolved in 10 ml of anhydrous THF, were slowly dropped into the clear solution. After 15 minutes, water was added and acetic acid was added till acidic pH. The reaction mixture was extracted with AcOEt. The organic phase was washed with a NaCl saturated solution, dried on Na2SO4 and evaporated to dryness. The residue was purified by FC (eluent: hexane/AcOEt 8:2). 2.6 g of a clear oil were obtained (yield 93%); 1H-NMR (200 MHz, CDCl3)δ: 0.86 (t, 3H), 1.15-1.62 (m, 4H), 2.25-2.65 (m, 2H), 3.20 (d, 2H), 3.63 (s, 3H), 3.71 (s, 3H), 3.84 (t, 1H), 7.12-7.58 (m, 7H), 7.78 (dd, 1H).

Workup

  1. additionwere dropped into a suspension
  2. additionwere slowly dropped into the clear solution
  3. extractionThe reaction mixture was extracted with AcOEt
  4. washThe organic phase was washed with a NaCl saturated solution
  5. customdried on Na2SO4
  6. customevaporated to dryness
  7. customThe residue was purified by FC (eluent: hexane/AcOEt 8:2)

Sources & evidence

ORD record
ord-653b84859dc94982ab5f2269628ea5a7
Source dataset
uspto-grants-1996_10
Patent number
US05565464

Reaction notes

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