Sodium Bicarbonate → HCID 68743336, compound

HRID 1893137Notes

Reaction equation

HRID 1893137 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]([S:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[CH:45]=O)[CH:29]=1.C(=O)(O)[O-].[Na+]>CCOCC>[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]([S:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[CH:45]=[CH2:2])[CH:29]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 638159Methyltriphenylphosphonium iodideHCID 21198703HCID 21198703, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 68743336HCID 68743336, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl triphenylphosphonium iodide (1.56 g, 3.87 mmol) was dissolved in 25 mL ether in a 50 ml round-bottom flask at 0° C. under dry nitrogen. To the mixture was added in one portion potassium tert-butoxide (0.46 g, 4.15 mmol) and was stirred for 10 min at room temperature. 2-(3-naphtylsulfanyl)benzenecarbaldehyde (0.73 g, 2.77 mmol) was added in one portion at 0° C. and the reaction mixture was stirred for additional 2.5 h at room temperature. The mixture was added to 50 mL, of saturated sodium bicarbonate solution, and extracted with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The light yellow oil of the crude product was further purified by chromatography on silica gel using 9:1 petroleum ether 60-80: ether as eluent to afford a colorless oil (0.58 g, 81%). 1H-NMR (500 MHz, CDCl3): δ 5.35 (dd, J=1.3, 11.0 Hz, 1H), 5.77 (dd, J=1.3, 17.5 Hz, 1H), 7.24-7.51 (m, 7H), 7.67-7.81 (m, 5H) ppm. 13C-NMR (125 MHz, CDCl3): δ 116.28, 125.85, 126.20, 126.50, 127.22, 127.48, 127.68, 127.97, 128.24, 128.49, 128.70, 131.91, 132.81, 133.72, 133.78, 133.81, 134.52, 139.71 ppm. E1-MS: m/z M+ Calc. 262.3, found 262.2.

Workup

  1. stirringthe reaction mixture was stirred for additional 2.5 h at room temperature
  2. extractionextracted with 3×50 mL portions of ether
  3. dry with materialThe extracts were dried with magnesium sulfate
  4. customevaporated
  5. customThe light yellow oil of the crude product was further purified by chromatography on silica gel using 9:1 petroleum ether 60-80

Sources & evidence

ORD record
ord-2e76cf7c52de45319f882b600fa8b774
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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