Tetrahydrofuran → HCID 58231725, compound

HRID 408078Notes

Reaction equation

HRID 408078 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:23]3[C:18](=[CH:19][C:20]([C:24]4[C:29]5[S:30][C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=6[C:28]=5[CH:27]=[CH:26][CH:25]=4)=[CH:21][CH:22]=3)[CH:17]=[CH:16][C:15]=2[OH:37])=[CH:3][CH:2]=1.[CH2:38]1C[O:41][CH2:40][CH2:39]1.C(N(CC)CC)C.C(Cl)(=O)C=C>O.C(OCC)(=O)C>[C:40]([O:37][C:15]1[CH:16]=[CH:17][C:18]2[C:23](=[CH:22][CH:21]=[C:20]([C:24]3[C:29]4[S:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[C:28]=4[CH:27]=[CH:26][CH:25]=3)[CH:19]=2)[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:41])[CH:39]=[CH2:38]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 67087534HCID 67087534, compound

Product 1

HCID 58231725HCID 58231725, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.8 g of the thus obtained 1,6-bis(4-dibenzothiophenyl)-2-naphthol is placed in a round bottom flask; 30 mL of THF is added to form a transparent solution; after ice cooling the flask, 0.58 g of triethylamine is added; 0.48 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 1.8 g (yield: 90%) of the foregoing white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 5.66 (dd=1.2 & 10.4 Hz, 1H), 5.94 (dd=10.4 & 17.2 Hz, 1H), 6.18 (dd=1.2 & 17.2 Hz, 1H), 7.37 to 7.60 (m, 10H), 7.67 to 7.74 (m, 2H), 7.77 to 7.82 (m, 1H), 8.07 (d=8.8 Hz, 1H), 8.10 to 8.24 (m, 4H), 8.15 (d=1.6 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)

Sources & evidence

ORD record
ord-ba55e5e340b34d1e881c06108c78a7d7
Source dataset
uspto-grants-2014_06
Patent number
US08758960B2

Reaction notes

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