Triethylamine → HCID 21997124, compound

HRID 703765Notes

Reaction equation

HRID 703765 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:27])[C:24]([CH3:26])=[CH2:25]>C(Cl)Cl.C(OCC)C>[C:23]([O:13][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:15][CH:14]=1)(=[O:27])[C:24]([CH3:26])=[CH2:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 11413119Benzenemethanol, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-

Product 1

HCID 21997124HCID 21997124, compoundYield 8.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 62.4 g (0.3 mol) of 4-tetrahydropyranyloxy benzyl alcohol and 58.5 mL of triethylamine in 225 mL of methylene chloride and 225 mL of diethyl ether cooled in an ice bath was added dropwise 31.9 mL (0.33 mol) of methacrylyl chloride at a rate such that the temperature did not exceed 30° C. After 3.5 hr, the mixture was filtered, and the filtrate was evaporated. The residual oil was treated with ether and triethylamine and washed with water. The organic layer was dried (sodium sulfate) and evaporated to a yellow oil, which, on standing, gradually crystallized. The crystals were rinsed with a small amount of methanol to give 7.3 g of colorless crystals, m.p. 36-36.7° C. The product can be recrystallized from hexane at low temperature. 1H NMR (360 MHz, THF-d8): 1.5-1.82 (m's, 6H, CH2), 1.90 (m, 3H, CH3C=), 3.5 (m, 1H, OCH 2), 3.8 (m, 1H, OCH2), 5.07 (s, 2H, ArCH2OOC), 5.40 (t, J=3, 1H, OCHO), 5.52 (m, 1H, =CH), 6.05 (m, 1H, =CH), 7.0 (m, 2H, ArH), 7.27 (m, 2H, ArH).

Workup

  1. customdid not exceed 30° C
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated
  4. additionThe residual oil was treated with ether and triethylamine
  5. washwashed with water
  6. dry with materialThe organic layer was dried (sodium sulfate)
  7. customevaporated to a yellow oil, which
  8. customgradually crystallized
  9. washThe crystals were rinsed with a small amount of methanol

Sources & evidence

ORD record
ord-15f8b1fa39f74c9c831adb7c6a6d369a
Source dataset
uspto-grants-1991_01
Patent number
US04985332

Reaction notes

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