Sodium Bicarbonate → HCID 86641473, compound

HRID 1893141Notes

Reaction equation

HRID 1893141 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[K].[O-]CCCC.[CH:28]1[C:41]2[C:42]3=[C:43]4[C:38](=[CH:39][CH:40]=2)[CH:37]=[CH:36][CH:35]=[C:34]4[CH:33]=[CH:32][C:31]3=[C:30]([S:44][C:45]2[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=2[CH:47]=O)[CH:29]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:28]1[C:41]2[C:42]3=[C:43]4[C:38](=[CH:39][CH:40]=2)[CH:37]=[CH:36][CH:35]=[C:34]4[CH:33]=[CH:32][C:31]3=[C:30]([S:44][C:45]2[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=2[CH:47]=[CH2:2])[CH:29]=1

Participants

7

Reactant 5

HCID 516892Sodium BicarbonateHCID 638159Methyltriphenylphosphonium iodideHCID 5462222PotassiumHCID 12476378Butan-1-olateHCID 86641472HCID 86641472, compound

Product 1

HCID 86641473HCID 86641473, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl triphenylphosphonium iodide (250 mg, 0.62 mmol) was dissolved in 20 mL of dry THF at 0° C. under dry nitrogen. To the mixture was added in one portion potassium tort-butoxide (75 mg, 0.66 mmol) and was stirred for 10 min at room temperature. 2-(pyrene-3-ylthio)-benzaldehyde (150 mg, 0.44 mmol) was added in one portion at 0° C. and the reaction mixture was stirred for additional 5 h at room temperature. The mixture was added to 50 mL of saturated sodium bicarbonate solution, and extracted with 3 portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using 20:1 petroleum ether (60-80):EtOAc as eluent to afford a yellow solid (100 mg, 70%). 1H-NMR (500 MHz, CDCl3): δ 5.36 (dd, J=1.3, 11.3 Hz, 1H), 5.77 (dd, J=1.3, 17.4 Hz, 1H), 6.92 (dd, J=1.3, 7.8 Hz, 1H), 7.02-7.05 (m, 1H), 7.20-7.23 (m, 1H), 7.37 (dd, J=10.8, 17.4 Hz, 1H), 7.61 (dd, J=1.3, 7.8 Hz, 1H), 7.94 (d, J=8.2 Hz, 1H), 8.01-8.22 (m, 8H), 8.61 (d, J=9.5 Hz, 1H). 13C-NMR (125 MHz, CDCl3): δ 116.4, 124.4, 124.5, 125.2, 125.3, 125.5, 126.1, 126.2, 126.9, 127.2, 127.8, 128.4, 128.5, 128.9, 130.9, 131.0, 131.1, 131.2, 131.4, 134.3, 137.9. EI-MS: m/z M+ Calculated 336.1, found 336.1.

Workup

  1. stirringthe reaction mixture was stirred for additional 5 h at room temperature
  2. extractionextracted with 3 portions of ether
  3. dry with materialThe extracts were dried with magnesium sulfate
  4. customevaporated
  5. customThe crude product was further purified by chromatography on silica gel using 20:1 petroleum ether (60-80)

Sources & evidence

ORD record
ord-f616b81912f14d18a0e284788bfd2348
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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