Dichloromethane → HCID 54028035, compound

HRID 931876Notes

Reaction equation

HRID 931876 reaction equation
C(Cl)Cl.[CH3:4][C:5]1([CH3:12])[O:10][CH2:9][CH:8]([OH:11])[CH2:7][O:6]1.[C:13](Cl)(=[O:17])[C:14]([CH3:16])=[CH2:15]>C(N(CC)CC)C>[C:13]([O:11][CH:8]1[CH2:9][O:10][C:5]([CH3:12])([CH3:4])[O:6][CH2:7]1)(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 13528Methacryloyl chlorideHCID 110298842,2-Dimethyl-1,3-dioxan-5-ol

Product 1

HCID 54028035HCID 54028035, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a CH2Cl2 (200 mL) solution of 2,2-dimethyl-1,3-dioxan-5-ol (17.0 g, 0.13 mol) at 0° C., triethylamine (20 mL) was added slowly. The reaction flask was flushed with nitrogen for 5 minutes. Methacryloyl chloride (13.5 g, 0.13 mol) was added dropwise. The reaction mixture was stirred at room temperature for 3 hours, then filtered, washed with a water solution of NaHCO3 (1M, 2×200 mL) and distilled water (2×200 mL). The filtrate was dried over MgSO4. 1,4-hydroquinone (10 mg) was added as an inhibitor and solvent was removed. The oil was dissolved in ethyl acetate (50 mL) and passed through a silica gel plug. Solvent was removed and the product was purified by distillation, yielding a colorless oil product (18.5 g, 71%). 1H NMR (300 MHz, CDCl3) δ 1.38 (s, 3H), 1.41 (s, 3H), 1.92 (s, 3H), 3.77 (d, 1H), 3.82 (d, 1H), 4.05 (d, 1H), 4.10 (d, 1H), 4.71 (m, 1H), 5.56 (s, 1H), 6.12 (s, 1H). 13C NMR (75.5 MHz, CDCl3) δ 19.2, 20.6, 23.0, 61.6, 63.2, 99.3, 123.2, 124.5, 138.1.

Workup

  1. customThe reaction flask was flushed with nitrogen for 5 minutes
  2. filtrationfiltered
  3. washwashed with a water solution of NaHCO3 (1M, 2×200 mL)
  4. distillationdistilled water (2×200 mL)
  5. dry with materialThe filtrate was dried over MgSO4
  6. addition1,4-hydroquinone (10 mg) was added as an inhibitor and solvent
  7. customwas removed
  8. dissolutionThe oil was dissolved in ethyl acetate (50 mL)
  9. customSolvent was removed
  10. distillationthe product was purified by distillation

Sources & evidence

ORD record
ord-edf49ca206ec4f50b77942023d833fbd
Source dataset
uspto-grants-2016_03
Patent number
US09298093B2

Reaction notes

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