2,3-Dihydrofuran → 2-Tetrahydrofuranyl acrylate

HRID 483961Notes

Reaction equation

HRID 483961 reaction equation
[O:1]1[CH:5]=[CH:4][CH2:3][CH2:2]1.C1([CH:20]=[CH:21][C:22]([OH:24])=[O:23])C2NC3C(=CC=CC=3)SC=2C=CC=1.C=CC1C=CN=CC=1.Cl>>[C:22]([O:24][CH:5]1[CH2:4][CH2:3][CH2:2][O:1]1)(=[O:23])[CH:21]=[CH2:20]

Participants

4

Reactant 3

HCID 709342,3-DihydrofuranHCID 122453074-Vinylpyridine hydrochlorideHCID 73845302phenothiazine Acrylic acid

Product 1

HCID 144548152-Tetrahydrofuranyl acrylate

Procedure

To a 100 mL 3-neck round bottom flask equipped with a stir bar, condenser, and addition funnel was added 39 mL of dihydrofuran (FW 70.09, d=0.927), and 0.18 g of phenothiazine Acrylic acid (19 mL, FW 72.06, d=1.05) was added dropwise slowly with stirring. A mild exotherm (55° C.) occurred. After cooling to room temperature, 0.415 g of poly(4-vinylpyridine hydrochloride) was added and the reaction was stirred overnight. The acid catalyst was then filtered off and 0.2 g each of calcium hydride and potassium carbonate was added to the filtrate. After removal of excess dihydrofuran on a rotovap, 10 mg of DPPH (2,2-diphenyl-1-picrylhydrazyl hydrate) was added and the slurry was vacuum distilled at 200 mtorr at 26° C. to give 26.0 g of 2-tetrahydrofuranyl acrylate.

Workup

  1. customTo a 100 mL 3-neck round bottom flask equipped with a stir bar, condenser, and addition funnel
  2. additionwas added dropwise slowly
  3. customA mild exotherm (55° C.)
  4. stirringthe reaction was stirred overnight
  5. filtrationThe acid catalyst was then filtered off
  6. addition0.2 g each of calcium hydride and potassium carbonate was added to the filtrate
  7. customAfter removal of excess dihydrofuran on a rotovap, 10 mg of DPPH (2,2-diphenyl-1-picrylhydrazyl hydrate)
  8. additionwas added
  9. distillationdistilled at 200 mtorr at 26° C.

Sources & evidence

ORD record
ord-09e57485b845444892ecd054803b8e13
Source dataset
uspto-grants-1993_07
Patent number
US05229244

Reaction notes

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