Dichloromethane → 3-(1,3-Dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propyl acetate

HRID 1062506Notes

Reaction equation

HRID 1062506 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][CH:9]([CH:11]1[CH2:16][CH:15]2[CH2:17][CH:12]1[CH:13]=[CH:14]2)[OH:10].[C:18](OC(=O)C)(=[O:20])[CH3:19].C(Cl)Cl.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.O>[C:18]([O:10][CH:9]([CH:11]1[CH2:16][CH:15]2[CH2:17][CH:12]1[CH:13]=[CH:14]2)[CH2:8][CH2:7][CH:2]1[O:3][CH2:4][CH2:5][CH2:6][O:1]1)(=[O:20])[CH3:19]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 222810373-(1,3-Dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propanol

Product 1

HCID 222810363-(1,3-Dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propyl acetateYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of 15.0 g of 3-(1,3-dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propanol, 9.6 g of acetic anhydride, 100 mg of 4-dimethylaminopyridine and 50 ml of methylene chloride, 10.2 g of triethylamine was added dropwise over 30 minutes at 20° C. Stirring was continued for 30 minutes whereupon 10 g of water was added to stop reaction. Stirring was continued for a further 30 minutes whereupon water was added to the reaction solution, which was extracted with hexane. The organic layer was successively washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 16.9 g of 3-(1,3-dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propyl acetate (boiling point 125° C./53 Pa, yield 96%).

Workup

  1. additionwas added dropwise over 30 minutes at 20° C
  2. additionwas added
  3. customreaction
  4. stirringStirring
  5. additionwas added to the reaction solution, which
  6. extractionwas extracted with hexane
  7. washThe organic layer was successively washed with water and saturated sodium chloride water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuum
  10. distillationIt was further purified by vacuum distillation

Sources & evidence

ORD record
ord-ab4caa75d6b04b328cec8aae0bf78847
Source dataset
uspto-grants-2005_11
Patent number
US06962767B2

Reaction notes

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