Tetrahydrofuran → HCID 58231716, compound

HRID 408079Notes

Reaction equation

HRID 408079 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[C:22]3[C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[S:19][C:18]=3[C:17]([OH:27])=[C:16]([C:28]3[C:33]4[S:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[C:32]=4[CH:31]=[CH:30][CH:29]=3)[CH:15]=2)=[CH:3][CH:2]=1.[CH2:41]1C[O:44][CH2:43][CH2:42]1.C(N(CC)CC)C.C(Cl)(=O)C=C>O.C(OCC)(=O)C>[C:43]([O:27][C:17]1[C:18]2[S:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[C:22]=2[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:15][C:16]=1[C:28]1[C:33]2[S:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:44])[CH:42]=[CH2:41]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 67087524HCID 67087524, compound

Product 1

HCID 58231716HCID 58231716, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.6 g of the thus obtained 1,3-bis(4-dibenzothiophenyl)-4-hydroxydibenzothiophene is placed in a round bottom flask; 35 mL of THF is added to form a transparent solution; after ice cooling the flask, 0.47 g of triethylamine is added; 0.38 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. 15 mL of water is added; the mixture is vigorously stirred; and 30 mL of ethyl acetate and 15 mL of saturated salt water are then added, thereby separating an aqueous solution. An organic phase is washed with saturated salt water and dried upon application of magnesium sulfate. The resulting mixture is concentrated by filtration with a filter paper; and a major product is separated by a silica gel column (eluate: hexane/dichloromethane mixture), thereby obtaining the foregoing brown solid. This is washed with a mixed solvent of 20 mL of dichloromethane and 60 mL of hexane and then dried to obtain 1.1 g (yield: 63%) of the foregoing pale brown solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 5.90 (dd=1.2 & 10.4 Hz, 1H), 6.16 (dd=10.4 & 17.2 Hz, 1H), 6.47 (dd=1.2 & 17.2 Hz, 1H), 6.89 (d=7.6 Hz, 1H), 6.98 (dt=1.2 & 7.6 Hz, 1H), 7.30 to 7.35 (m, 1H), 7.40 to 7.58 (m, 6H), 7.62 to 7.68 (m, 2H), 7.73 to 7.84 (m, 4H), 8.12 to 8.18 (m, 2H), 8.25 (dd=0.8 & 7.6 Hz, 1H), 8.31 (dd=1.2 & 7.6 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. customseparating an aqueous solution
  6. washAn organic phase is washed with saturated salt water
  7. dry with materialdried upon application of magnesium sulfate
  8. concentrationThe resulting mixture is concentrated by filtration with a filter paper
  9. customand a major product is separated by a silica gel column (eluate: hexane/dichloromethane mixture)
  10. customobtaining the foregoing brown solid
  11. washThis is washed with a mixed solvent of 20 mL of dichloromethane and 60 mL of hexane
  12. customdried

Sources & evidence

ORD record
ord-7453724d79d147a9a35e88d17be0b854
Source dataset
uspto-grants-2014_06
Patent number
US08758960B2

Reaction notes

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