1,3-Propanediol → HCID 59856354, compound

HRID 1845708Notes

Reaction equation

HRID 1845708 reaction equation
[H-].[Na+].Br[CH2:4][C:5]1[CH:6]=[C:7]([B:13]2[O:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH:8]=[C:9]([CH2:11][Br:12])[CH:10]=1.[CH2:19]([OH:23])[CH2:20][CH2:21][OH:22]>C(#N)C>[Br:12][CH2:11][C:9]1[CH:10]=[C:5]([CH:6]=[C:7]([B:13]2[O:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH:8]=1)[CH2:4][O:22][CH2:21][CH2:20][CH2:19][OH:23]

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 59856353HCID 59856353, compound

Product 1

HCID 59856354HCID 59856354, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An oven-dried, 250-mL round bottom flask equipped with a magnetic stirring bar and reflux condenser was cooled under argon and charged with NaH (0.800 g of 60% in mineral oil, 20 mmols). The powder was washed with pentane (3×100 mL) and dried in vacuum. Acetonitrile (50 mL) was added by syringe and the mixture stirred at room temperature. 1,3-Propane diol (10 mL) was added dropwise over ten min. to form a white insoluble precipitate. The suspension was vigorously stirred for one hour at which time 20 mL was taken up by syringe and added dropwide to a 250-mL round bottom flask charged with 2-(3,5-Bis-bromomethyl-phenyl)-(1,3,2)dioxaborinane (2.865 g, 8.2 mmols) and acetonitrile (50 mL). The mixture was stirred for 12 hr at room temperature. A reflux condenser was attached along with a vacuum adapter and the reaction mixture was heated to reflux under argon for two hours. The acetonitrile was removed in vacuo and the residue purified by flash chromatography (EtOAc:hexane, 2:1). Removal of solvents gave a suspension of white solids in a yellow oil, which when analyzed by thin layer chromatography showed no starting material. The crude mixture containing 1,3-propane diol was used without further purification.

Workup

  1. customAn oven-dried, 250-mL round bottom flask equipped with a magnetic stirring bar
  2. temperaturereflux condenser
  3. temperaturewas cooled under argon
  4. washThe powder was washed with pentane (3×100 mL)
  5. customdried in vacuum
  6. additionAcetonitrile (50 mL) was added by syringe
  7. addition1,3-Propane diol (10 mL) was added dropwise over ten min.
  8. customto form a white insoluble precipitate
  9. stirringThe suspension was vigorously stirred for one hour at which time 20 mL
  10. customwas taken up by syringe
  11. additionadded dropwide to a 250-mL round bottom flask
  12. stirringThe mixture was stirred for 12 hr at room temperature
  13. customA reflux condenser was attached along with a vacuum adapter
  14. temperaturethe reaction mixture was heated
  15. temperatureto reflux under argon for two hours
  16. customThe acetonitrile was removed in vacuo
  17. customthe residue purified by flash chromatography (EtOAc:hexane, 2:1)
  18. customRemoval of solvents
  19. customgave
  20. additiona suspension of white solids in a yellow oil, which when
  21. customwas used without further purification

Sources & evidence

ORD record
ord-3d9a4e8028b2441f8052729deb0b048c
Source dataset
uspto-grants-2015_02
Patent number
US08951503B2

Reaction notes

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