Water → HCID 68818912, compound

HRID 1784459Notes

Reaction equation

HRID 1784459 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[C:27]([O:33][CH2:34][O:35][CH3:36])[CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>O1CCCC1>[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:27]([O:33][CH2:34][O:35][CH3:36])[CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 178620602-(Methoxymethoxy)-4-(phenylmethoxy)benzaldehyde

Product 1

HCID 68818912HCID 68818912, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 55% sodium hydride dispersion in mineral oil (1.57 g, 36.0 mmol) in tetrahydrofuran (100 ml) was added ethyl diethylphosphonoacetate (7.17 g, 32.0 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 30 minutes at 0° C. under a nitrogen atmosphere. Subsequently, a solution of 4-benzyloxy-2-methoxymethoxy-benzaldehyde (7.46 g, 27.4 mmol) obtained in step (b) of Example 197 in tetrahydrofuran was added at 0° C. with stirring, and the resulting mixture was stirred for 2 hours at 0° C. under a nitrogen atmosphere. After stirring, water (200 ml) was added, and the resulting mixture was extracted with ethyl acetate (200 ml×2). The organic layer was washed successively with water (100 ml×1) and saturated aqueous sodium chloride solution (100 ml×1), dried-over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (5:1-1:1) as the eluent to afford the title compound (9.32 g, yield: 99%) as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes at 0° C. under a nitrogen atmosphere
  2. stirringwith stirring
  3. stirringthe resulting mixture was stirred for 2 hours at 0° C. under a nitrogen atmosphere
  4. stirringAfter stirring
  5. extractionthe resulting mixture was extracted with ethyl acetate (200 ml×2)
  6. washThe organic layer was washed successively with water (100 ml×1) and saturated aqueous sodium chloride solution (100 ml×1), dried-over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto afford the crude product
  10. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-cfa6a4fe33564c42bbb76b0af6ce6fb0
Source dataset
uspto-grants-2009_03
Patent number
US07504393B2

Reaction notes

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