Hydrochloric Acid → HCID 22730196, compound

HRID 1785839Notes

Reaction equation

HRID 1785839 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)=[C:5]([O:19][CH3:20])[CH:4]=1.[H-].[Na+].[CH3:23]I.Cl>C1COCC1.O1CCOCC1>[CH3:20][O:19][C:5]1[CH:4]=[C:3]([CH2:2][O:1][CH3:23])[CH:8]=[CH:7][C:6]=1[C:9]1[CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22730788HCID 22730788, compound

Product 1

HCID 22730196HCID 22730196, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 417A (142 mg, 0.5 mmol) in THF (3 mL) at room temperature was treated with 60% sodium hydride in oil (40 mg, 1.0 mmol) and methyl iodide (0.30 mmol), stirred for 30 minutes, adjusted to pH<7 with 4M HCl in dioxane (0.5 mL), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes to provide the desired product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1ce22d6cab7d4438bd93a5a0416d7bf2
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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