Ammonium Chloride → HCID 18968794, compound

HRID 398815Notes

Reaction equation

HRID 398815 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([C:9]1([CH:26]=O)[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=2[S:11][CH2:10]1)[CH3:8].[NH4+].[Cl-]>C1COCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:7]([C:9]1([CH:26]=[CH2:1])[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=2[S:11][CH2:10]1)[CH3:8]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 18968790HCID 18968790, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18968794HCID 18968794, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A 1.0M solution of potassium t-butoxide in THF (82 ml, Aldrich) was added to a suspension of methyl triphenylphosphonium bromide (29.0 g, Aldrich) in 250 ml of THF. After complete addition, the reaction mixture was refluxed for one hour, cooled with an ice bath and the product from step (e) (12.0 g) in 70 ml of THF was added. The reaction was stirred for 1 hr at room temperature, refluxed for 2.5 hr and then stirred at room temperature for 17 hr. Saturated NH4Cl(200 ml) was added, the organic layer was separated, dried and concentrated to give a red-orange oil. Chromatography on silica using hexanes/EtOAc (9:1) as eluant afforded the title product as a light orange oil (11.0 g). 1H NMR consistent with the proposed structure.

Workup

  1. additionAfter complete addition
  2. temperaturethe reaction mixture was refluxed for one hour
  3. temperaturecooled with an ice bath
  4. temperaturerefluxed for 2.5 hr
  5. stirringstirred at room temperature for 17 hr
  6. customthe organic layer was separated
  7. customdried
  8. concentrationconcentrated
  9. customto give a red-orange oil

Sources & evidence

ORD record
ord-1b06ad87ed87489587b1f3a849de5fe0
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Reaction notes

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