Hydrochloric Acid → HCID 57449972, compound

HRID 333832Notes

Reaction equation

HRID 333832 reaction equation
C[C:2]([O-:5])(C)C.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([N:14]([CH2:18][CH:19]=[CH2:20])[CH2:15][CH:16]=[CH2:17])[CH:11]=[CH:10][C:9]=1[C:21](=O)[CH3:22].[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1.O>[Cl:7][C:8]1[CH:13]=[C:12]([N:14]([CH2:18][CH:19]=[CH2:20])[CH2:15][CH:16]=[CH2:17])[CH:11]=[CH:10][C:9]=1[CH:21]([CH3:22])[CH:2]=[O:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723798Methoxymethyl-triphenylphosphonium chloride3×HCID 23665647Potassium tert-butoxide3×HCID 57421343HCID 57421343, compound

Product 1

HCID 57449972HCID 57449972, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butylate (1.33 g) was added to a solution of 1-(2-chloro-4-diallylamino-phenyl)-ethanone (2.36 g) and (methoxymethyl)triphenylphosphonium chloride ([CAS Reg. No. 4009-98-7], 3.75 g) in THF (55 ml). The mixture was stirred for 1 h at room temperature. Additional (methoxymethyl)triphenylphosphonium chloride (324 mg) and potassium tert-butylate (133 mg) were added and stirring was continued for 1 h. More (methoxymethyl)triphenylphosphonium chloride (324 mg) and potassium tert-butylate (133 mg) was added and stirring was continued for 30 min. HCl (25% aq, 15 ml) was added. The mixture was stirred for 1 h at room temperature and then for 45 min at 50° C. Water (100 ml) was added, neutralized carefully by addition of sodium bicarbonate, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane 0:100-20:80) to give the title compound as a light yellow oil (2.1 g). MS (m/e)=264.1 [M+H+].

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. stirringstirring
  4. waitwas continued for 30 min
  5. stirringThe mixture was stirred for 1 h at room temperature
  6. waitfor 45 min at 50° C
  7. extractionextracted with DCM
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane 0:100-20:80)

Sources & evidence

ORD record
ord-15065d6898e945dca839b53f2ddf1dba
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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