Dichloromethane → HCID 58231726, compound

HRID 408070Notes

Reaction equation

HRID 408070 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[C:14]([C:16]2[S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[CH:20]=2)[CH:13]=[CH:12][C:11]=1[OH:25].C(Cl)Cl.[O:29]1C[CH2:32][CH2:31][CH2:30]1.C(Cl)(=O)C=C>O.C(N(CC)CC)C>[C:30]([O:25][C:11]1[CH:12]=[CH:13][C:14]([C:16]2[S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[CH:20]=2)=[CH:15][C:10]=1[C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1)(=[O:29])[CH:31]=[CH2:32]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 13140Acryloyl chlorideHCID 67087337HCID 67087337, compound

Product 1

HCID 58231726HCID 58231726, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

1.31 g of the thus obtained 2,4-bis(2-benzothiophenyl)phenol is placed in a round bottom flask; 20 mL of methylene chloride and 2 mL of tetrahydrofuran are added to form a transparent solution; after ice cooling the flask, 0.44 g of triethylamine is added; 0.39 g of acryloyl 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 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=90/10 (volume ratio)) to concentrate a component having an Rf of 0.20, thereby obtaining 1.0 g (yield: 66%) of the foregoing white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 6.06 (dd=1.2 & 10.8 Hz, 1H), 6.38 (dd=10.8 & 17.2 Hz, 1H), 6.64 (dd=1.2 & 17.2 Hz, 1H), 7.31 to 7.40 (m, 5H), 7.59 (s, 2H), 7.70 to 7.85 (m, 5H), 8.05 (d=2.4 Hz, 1H)

Workup

  1. customto form a transparent solution
  2. additionafter adding the whole
  3. customis returned to room temperature
  4. stirringthe mixture is vigorously stirred
  5. customan aqueous layer is then removed
  6. washthe aqueous layer is washed with methylene chloride
  7. dry with materialand the mixture is dried upon application of magnesium sulfate
  8. concentrationThe resulting mixture is concentrated by filtration with a filter paper
  9. customand the concentrate is separated by a silica gel column (eluate: hexane/ethyl acetate=90/10 (volume ratio))
  10. concentrationto concentrate a component

Sources & evidence

ORD record
ord-e4c7fd6befcb490fb115d38b737f4983
Source dataset
uspto-grants-2014_06
Patent number
US08758960B2

Reaction notes

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