Ammonium Chloride → HCID 54559612, compound

HRID 2165189Notes

Reaction equation

HRID 2165189 reaction equation
C([CH2:3][CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)=O.[Cl-].[NH4+].S(=O)(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:16][O:15][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[C:5]([CH2:4][CH2:3][CH:12]=[CH:13][O:15][CH3:16])[CH:14]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 516919Sodium BisulfateHCID 14537110HCID 14537110, compound

Product 1

HCID 54559612HCID 54559612, compoundYield 260.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 50 ml oven-dried 2-necked (14/20) round bottom flask, equipped with magnetic stirring bar, nitrogen inlet and serum cap is charged with methoxymethyltriphenylphosphonium chloride (90%) (2.5 g). This material is suspended in 10 ml tetrahydrofuran and the resulting mixture is placed under a nitrogen atmosphere and cooled to 0°-5° C. n-Butyllithium reagent (1.65 M in hexane, 4.0 ml) is added dropwise to the stirred mixture via syringe over 2-3 min. The solids gradually dissolve to give a deep red colored solution (some solids remain). This solution is stirred at 0°-5° C. for 30 min and then is treated with a solution of 2-(2-formylethyl)-4-methoxy-1-[(tetrahydro-2H-pyran-2-yl)oxy]naphthalene (0.958 g) in 5 ml tetrahydrofuran in one portion. The resulting deep red colored solution is stirred at 0°-5° C. for 15 min at which time TLC analysis indicates no remaining starting material. The solution is poured into saturated aqueous ammonium chloride, the pH adjusted to 7 with 10% sodium bisulfate and this mixture extracted first with Skellysolve B and then with ether. Each of these extracts is washed two times with water, dried with magnesium sulfate, filtered and concentrated. TLC analysis of the ether extract indicates the presence of the product mixture suggesting that the Skellysolve B extraction is not efficient. The separate extracts are combined to give 1.36 g of the title compound mixture.

Workup

  1. dry with materialA 50 ml oven-dried 2-necked (14/20) round bottom flask
  2. customequipped with magnetic stirring bar, nitrogen inlet
  3. customserum cap
  4. additionis charged with methoxymethyltriphenylphosphonium chloride (90%) (2.5 g)
  5. temperaturecooled to 0°-5° C. n-Butyllithium reagent (1.65 M in hexane, 4.0 ml)
  6. additionis added dropwise to the stirred mixture via syringe over 2-3 min
  7. dissolutionThe solids gradually dissolve
  8. customto give a deep red colored solution (some solids
  9. stirringThe resulting deep red colored solution is stirred at 0°-5° C. for 15 min at which time TLC analysis
  10. extractionthis mixture extracted first with Skellysolve B
  11. washEach of these extracts is washed two times with water
  12. dry with materialdried with magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. extractionTLC analysis of the ether extract
  16. extractionsuggesting that the Skellysolve B extraction

Sources & evidence

ORD record
ord-79e0f16815e248bf88dbc7ce71d6c5b8
Source dataset
uspto-grants-1990_07
Patent number
US04939169

Reaction notes

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