Tetrahydrofuran → 5808-99-1

HRID 626442Notes

Reaction equation

HRID 626442 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:17]1[CH2:21]O[CH2:19][CH2:18]1.C1(C=O)CC1>CN(C=O)C.O>[CH:17]1([CH:21]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 123114Cyclopropanecarboxaldehyde

Product 1

HCID 534018525808-99-1

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

At 0° C., 13.0 ml (64.85 mmol) of ethyl diethylphosphonoacetate were added dropwise to a suspension of 2.59 g (64.85 mmol) of sodium hydride (60% in mineral oil) in 110 ml of abs. THF. After 30 min, the mixture was warmed to RT and, after cooling again to 0° C., 5.3 ml (71.34 mmol) of cyclopropanecarboxaldehyde were added dropwise. After the end of the addition, the reaction mixture was warmed to RT and diluted with 35 ml of DMF. The mixture was stirred at RT overnight and then added to water. The mixture was extracted three times with ethyl acetate. The combined organic phases were concentrated under reduced pressure and the crude product was purified by filtration through silica gel (mobile phase cyclohexane/ethyl acetate 10:1→6:1). This gave 8.53 g of the target product (93.8% of theory).

Workup

  1. temperatureafter cooling again to 0° C.
  2. additionAfter the end of the addition
  3. temperaturethe reaction mixture was warmed to RT
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. concentrationThe combined organic phases were concentrated under reduced pressure
  6. filtrationthe crude product was purified by filtration through silica gel (mobile phase cyclohexane/ethyl acetate 10:1→6:1)

Sources & evidence

ORD record
ord-629f24e922994f8a9e8f0bc6ae0776f1
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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