Dimethylformamide → ethyl (2E)-3-(oxolan-3-yl)prop-2-enoate

HRID 1524786

Reaction equation

HRID 1524786 reaction equation
[H-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.[O:8]1[CH2:12][CH2:11][CH:10]([CH:13]=O)[CH2:9]1.CN(C=[O:19])C>O>[O:6]1[CH2:7][CH2:3][CH:4](/[CH:13]=[CH:10]/[C:9]([O:8][CH2:12][CH3:11])=[O:19])[CH2:5]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 1575683-Furancarboxaldehyde, tetrahydro-

Product 1

HCID 57478039ethyl (2E)-3-(oxolan-3-yl)prop-2-enoateYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 0° C. mixture of sodium hydride (60% in mineral oil) (382 mg, 9.40 mmol) in DMF (15.0 mL) (THF may also be used) was added triethyl phosphonoacetate (1.72 mL, 8.68 mmol) dropwise. The resulting mixture was warmed to room temperature and stirred for 30 minutes, then was re-cooled to 0° C., at which time a solution of tetrahydrofuran-3-carbaldehyde (724 mg, 7.23 mmol) in DMF (4.0 mL) was added dropwise. The resulting mixture was stirred at this temperature for 1.5 hours, at which time the mixture was diluted with water and the product was extracted with ether. The combined extracts were washed with water and brine, dried over sodium sulfate and the solvent removed in vacuo. Flash column chromatography (eluting with a gradient from 0-40% ethyl acetate in hexanes) afforded the product (640 mg, 52%).

Workup

  1. additionwas added dropwise
  2. stirringThe resulting mixture was stirred at this temperature for 1.5 hours, at which time the mixture
  3. extractionthe product was extracted with ether
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed in vacuo
  7. washFlash column chromatography (eluting with a gradient from 0-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-23cee04365c24b729e590a9c6b2290d9
Source dataset
uspto-grants-2015_07
Patent number
US09079912B2

Linked notes

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