Water → HCID 67087626, compound

HRID 408076Notes

Reaction equation

HRID 408076 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([C:14]2[CH:15]=[C:16](O)[CH:17]=[CH:18][CH:19]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30].[OH2:34]>C(Cl)Cl>[C:28]([O:32][C:19]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:4]1[C:5]2[S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=[CH:2][CH:3]=1)(=[O:34])[C:29]([CH3:31])=[CH2:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 67087638HCID 67087638, compound

Product 1

HCID 67087626HCID 67087626, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.65 g of 3-(4-dibenzothiophenyl)phenol obtained in Synthesis Example 5-(i) is placed and dissolved in 20 mL of methylene chloride; after ice cooling the flask, 0.28 g of triethylamine is added; 0.29 g of methacryloyl chloride is then added dropwise; after adding the whole, the temperature is returned to room temperature; and the mixture is stirred for 30 minutes. 10 mL of water is added; the mixture is vigorously stirred; an aqueous layer is then removed; the aqueous layer is washed with methylene chloride and then gathered with the original methylene chloride solution; and the mixture is dried upon application of magnesium sulfate. The resulting mixture is concentrated by filtration with a filter paper; and the concentrate is separated by a silica gel column (eluate: hexane/ethyl acetate=80/10 (volume ratio)) to concentrate a component having an Rf of 0.50, thereby obtaining 0.63 g (yield: 78%) of the foregoing white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 2.09 (s, 3H), 5.77 (dd=1.6 Hz, 1H), 6.39 (s, 1H), 7.21 (m, 1H), 7.45 to 7.55 (m, 6H), 7.62 to 7.64 (m, 1H), 7.82 to 7.85 (m, 1H), 8.14 to 8.19 (m, 2H)

Workup

  1. additionafter adding the whole
  2. customis returned to room temperature
  3. stirringthe mixture is vigorously stirred
  4. customan aqueous layer is then removed
  5. washthe aqueous layer is washed with methylene chloride
  6. dry with materialand the mixture is dried upon application of magnesium sulfate
  7. concentrationThe resulting mixture is concentrated by filtration with a filter paper
  8. customand the concentrate is separated by a silica gel column (eluate: hexane/ethyl acetate=80/10 (volume ratio))
  9. concentrationto concentrate a component

Sources & evidence

ORD record
ord-57a578a292874d88ae0bdf69c42fdcea
Source dataset
uspto-grants-2014_06
Patent number
US08758960B2

Reaction notes

Loading…