Sodium hydride → methyl 2-hydroxy-4-[(E)-2-(2-methoxy-4-propylphenyl)vinyl]benzoate

HRID 217432Notes

Reaction equation

HRID 217432 reaction equation
[H-].[Na+].[Si]([O:10][C:11]1[CH:20]=[C:19]([CH2:21]P(OCC)(OCC)=O)[CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14])(C(C)(C)C)(C)C.[CH3:30][O:31][C:32]1[CH:39]=[C:38]([CH2:40][CH2:41][CH3:42])[CH:37]=[CH:36][C:33]=1[CH:34]=O.[NH4+].[Cl-]>CN(C=O)C>[OH:10][C:11]1[CH:20]=[C:19](/[CH:21]=[CH:34]/[C:33]2[CH:36]=[CH:37][C:38]([CH2:40][CH2:41][CH3:42])=[CH:39][C:32]=2[O:31][CH3:30])[CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 58439044Methyl 2-{[tert-butyl(dimethyl)silyl]oxy}-4-[(diethoxyphosphoryl)methyl]benzoateHCID 866576402-Methoxy-4-propylbenzaldehyde

Product 1

HCID 58438893methyl 2-hydroxy-4-[(E)-2-(2-methoxy-4-propylphenyl)vinyl]benzoateYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of NaH (105.63 mg) in DMF (5.5 mL) was cooled to 0° C., and methyl 2-{[tert-butyl(dimethyl)silyl]oxy}-4-[(diethoxyphosphoryl)methyl]benzoate (550 mg) was added thereto. The reaction mixture was warmed to 25° C., then stirred for 1 hour, and cooled to 0° C. again, and 2-methoxy-4-propylbenzaldehyde (235.34 mg) was added thereto. The reaction mixture was warmed to 25° C. and then stirred for 15 hours. To the reaction liquid was added a saturated aqueous NH4Cl solution (50 mL), followed by extraction with EtOAc (50 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 70:30) to obtain methyl 2-hydroxy-4-[(E)-2-(2-methoxy-4-propylphenyl)vinyl]benzoate (304.2 mg) as a white solid.

Workup

  1. temperaturecooled to 0° C. again
  2. temperatureThe reaction mixture was warmed to 25° C.
  3. stirringstirred for 15 hours
  4. customTo the reaction liquid
  5. extractionfollowed by extraction with EtOAc (50 mL) three times
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 70:30)

Sources & evidence

ORD record
ord-3d2890c0615d41baa9d60607c419f415
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

Loading…