Tetrahydrofuran → HCID 58231720, compound

HRID 408077Notes

Reaction equation

HRID 408077 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:19]=[C:18]([C:20]3[C:25]4[S:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:24]=4[CH:23]=[CH:22][CH:21]=3)[CH:17]=[C:16]([C:33]3[C:38]4[S:39][C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=5[C:37]=4[CH:36]=[CH:35][CH:34]=3)[C:15]=2[OH:46])=[CH:3][CH:2]=1.[CH2:47]1C[O:50][CH2:49][CH2:48]1.C(N(CC)CC)C.C(Cl)(=O)C=C>ClCCl.O>[C:49]([O:46][C:15]1[C:14]([C:4]2[C:5]3[S:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)=[CH:19][C:18]([C:20]2[C:25]3[S:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:24]=3[CH:23]=[CH:22][CH:21]=2)=[CH:17][C:16]=1[C:33]1[C:38]2[S:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[C:37]=2[CH:36]=[CH:35][CH:34]=1)(=[O:50])[CH:48]=[CH2:47]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 67087350HCID 67087350, compound

Product 1

HCID 58231720HCID 58231720, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 g of the thus obtained 2,4,6-tris(4-dibenzothiophenyl)phenol is placed in a round bottom flask; 30 mL of THF is added to form a transparent solution; after ice cooling the flask, 0.4 g of triethylamine is added; 0.30 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. 30 mL of water is added; the mixture is vigorously stirred; and 100 mL of dichloromethane is then added, thereby separating an aqueous solution. The aqueous layer is washed with dichloromethane and then gathered with the original dichloromethane 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/dichloromethane mixture), thereby obtaining 0.9 g (yield: 59%) of the foregoing white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 5.44 (dd=1.2 & 10.4 Hz, 1H), 5.63 (dd=10.4 & 17.2 Hz, 1H), 5.96 (dd=1.2 & 17.2 Hz, 1H), 7.43 to 7.69 (m, 12H), 7.82 to 7.91 (m, 3H), 8.12 (s, 2H), 8.14 to 8.21 (m, 6H)

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. customseparating an aqueous solution
  6. washThe aqueous layer is washed with dichloromethane
  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/dichloromethane mixture)

Sources & evidence

ORD record
ord-4155779b0e884f668cd899bfeee220e4
Source dataset
uspto-grants-2014_06
Patent number
US08758960B2

Reaction notes

Loading…