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Tetrahydrofuran → HCID 89258928, compound

HRID 1352850
Notes
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Reaction equation

HRID 1352850 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[O:11][CH2:12][O:13][CH3:14].O1CCCC1.C(OP([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])(OCC)=O)C.[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:5][C:4]=1[O:11][CH2:12][O:13][CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 6401524-Methoxy-3-(methoxymethoxy)benzaldehyde

Product 1

HCID 89258928HCID 89258928, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

The compound (3.42 g, 17.4 mmol) of Example 9-1 was dissolved in N,N-dimethylformamide (30 ml) and tetrahydrofuran (30 ml) and then thereto were added ethyl diethylphosphonoacetate (3.91 g, 17.4 mmol) and sodium hydride (766 mg, 19.1 mmol). After stirring for 2 hours at 60° C., the mixture was allowed to cool to room temperature, and tetrahydrofuran was removed under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate-toluene (3:1). The organic layer was washed with water and an aqueous saturated sodium chloride solution in the order, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the subject compound (196 mg, 88.8%).

Workup

  1. temperatureto cool to room temperature
  2. customtetrahydrofuran was removed under reduced pressure
  3. additionTo the residue was added water
  4. extractionthe mixture was extracted with ethyl acetate-toluene (3:1)
  5. washThe organic layer was washed with water
  6. dry with materialan aqueous saturated sodium chloride solution in the order, dried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-659f8461c0a04467bd73eade0b2eecef
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07220773B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes