Hydrochloric Acid → HCID 86613496, compound

HRID 495281Notes

Reaction equation

HRID 495281 reaction equation
[OH:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.[CH3:20][O:21]C(Cl)Cl.[Sn](Cl)(Cl)(Cl)Cl.Cl>ClCCl.O>[CH:20]([C:5]1[C:6]([OH:8])=[CH:7][C:2]([OH:1])=[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 11230647HCID 11230647, compound

Product 1

HCID 86613496HCID 86613496, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

Compound 1 (0.25 g, 0.97 mmol) obtained in Example 1 was dissolved in dichloromethane (10 mL), and the solution was cooled to 4° C., and then dichloromethyl methyl ether (0.13 mL, 1.4 mmol) and tin(IV) chloride (0.17 g, 1.5 mmol) were added thereto and stirred at 4° C. for 5 minutes. Water (10 mL) and 3 mol/L hydrochloric acid (10 mL) were added to the reaction mixture, and extracted with chloroform (50 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The residue was purified through preparative thin-layer chromatography (n-hexane/ethyl acetate=1/2) and crystallized (n-hexane/ethyl acetate=1/2) to obtain Compound 55 (0.21 g, 85%).

Workup

  1. extractionextracted with chloroform (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated away under reduced pressure
  4. customThe residue was purified through preparative thin-layer chromatography (n-hexane/ethyl acetate=1/2)
  5. customcrystallized (n-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-9ef49f275f9845459afaabd33bc0ce6c
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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