Water → HCID 54328648, compound

HRID 1977983Notes

Reaction equation

HRID 1977983 reaction equation
[H-].[Na+].CCOP(OCC)([CH2:8][C:9]#[N:10])=O.[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][CH2:22][C:23]2=O)=[CH:18][CH:17]=1.O>O1CCCC1>[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][CH2:22][C:23]2=[CH:8][C:9]#[N:10])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 54328648HCID 54328648, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 60% sodium hydride (6.24 g, 156 mmol) in tetrahydrofuran (100 ml) was gradually added dropwise, under ice-cooling, diethyl cyanomethyl phosphonate (30.4 g, 172 mmol). The mixture was stirred for 15 minutes. To the reaction mixture was then added dropwise a solution of 7-methoxy-1-tetralone (25.2 g, 143 mmol) in THF (50 ml). The reaction mixture was heated for 3 hours under reflux. The reaction mixture was poured into water, and the organic layer was subjected to extraction with chloroform. The extract solution was washed with brine and water, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=9:1) to give the above-titled compound (a mixture of isomers) (28 g, yield 98%, oil). The above-titled compound (a mixture of isomers) was further purified by a silica gel column chromatography (hexane:ethyl acetate=98:2) to fractionally refine the respective isomers.

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was heated for 3 hours
  3. temperatureunder reflux
  4. extractionthe organic layer was subjected to extraction with chloroform
  5. washThe extract solution was washed with brine and water, which
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationby distilling off the solvent under reduced pressure
  8. customThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-0ad596cff77a42d88074dc84b1f4948b
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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