Triethyl phosphonoacetate → HCID 70340296, compound

HRID 2293103Notes

Reaction equation

HRID 2293103 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH:18]1[CH2:26][CH:27]=O>O1CCCC1>[CH2:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17][CH:18]1[CH2:26]/[CH:27]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 113786562-(2,3-dihydro-1H-inden-2-yl)acetaldehyde

Product 1

HCID 70340296HCID 70340296, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3.90 g of 63% sodium hydride was suspended in 60 ml of tetrahydrofuran, and 22.8 g of ethyl diethylphosphonoacetate dissolved in 100 ml of tetrahydrofuran was added dropwise to the suspension under water cooling. The mixture was stirred at the same temperature for 30 minutes. 13.58 g of 2-indanacetaldehyde dissolved in 100 ml of tetrahydrofuran was added dropwise to said mixture. The resulting mixture was stirred at the same temperature for 1 hour and further stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. After the ethyl acetate layer was washed and dried, the solvent was removed. The residue was purified by silica gel column chromatography (hexane-ethyl acetate (20:1)) to obtain 19.22 g of ethyl 2-indanecrotonate.

Workup

  1. additionwas added dropwise to the suspension under water cooling
  2. additionwas added dropwise
  3. stirringThe resulting mixture was stirred at the same temperature for 1 hour
  4. stirringfurther stirred at room temperature for 1 hour
  5. extractionextracted with ethyl acetate
  6. washAfter the ethyl acetate layer was washed
  7. customdried
  8. customthe solvent was removed
  9. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate (20:1))

Sources & evidence

ORD record
ord-7a69b85c610646df9f243a9d0e392359
Source dataset
uspto-grants-1997_11
Patent number
US05686452

Reaction notes

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