Sodium Bicarbonate → HCID 13082720, compound

HRID 1893130Notes

Reaction equation

HRID 1893130 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:28]([S:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH:37]=O)[CH3:29].C(=O)(O)[O-].[Na+]>CCOCC>[CH2:28]([S:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH:37]=[CH2:2])[CH3:29]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 638159Methyltriphenylphosphonium iodideHCID 130827262-(Ethylsulfanyl)benzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 13082720HCID 13082720, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl triphenylphosphonium iodide (1.57 g, 3.88 mmol) was dissolved in 25 mL ether in a 50 mL round-bottomed flask under dry nitrogen. To the mixture was added in one portion at 0° C. potassium tert-butoxide (0.47 g, 4.19 mmol) and it was stirred for 10 min at room temperature. 2-(ethylsulfanyl)benzenecarbaldehyde (2.77 mmol) was added in one portion at 0° C. and the reaction mixture was stirred until complete disappearance of the reactants (22 hr) at room temperature (followed by TLC). The mixture was added to 50 mL of saturated sodium bicarbonate solution, followed by extraction with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using petroleum ether 60-80 as eluent. Yield: 0.37 g, 81%, colorless oil. 1H NMR (200 MHz, CDCl3): δ 1.29 (t, J=7.3, 3H), 2.89 (q, J=7.3, 2H), 5.34 (dd, J1=10.9, J2=1.2, 1H), 5.69 (dd, J1=17.4, J2=1.2, 1H), 7.19-7.54 (m, 5H) ppm.

Workup

  1. stirringthe reaction mixture was stirred until complete disappearance of the reactants (22 hr) at room temperature (followed by TLC)
  2. extractionfollowed by extraction with 3×50 mL 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

Sources & evidence

ORD record
ord-6b5c71660f754e3f9bb3161888602bb9
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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