Hydrochloric Acid → HCID 58392085, compound

HRID 561426Notes

Reaction equation

HRID 561426 reaction equation
[OH:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)([CH3:9])[CH2:3][C:4](OCC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.ClCCl>[F:17][C:16]([F:18])([F:19])[C:13]1[CH:12]=[CH:11][C:10]([C:2]([OH:1])([CH3:9])[CH2:3][CH2:4][OH:5])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 55071304HCID 55071304, compound

Product 1

HCID 58392085HCID 58392085, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7.00 g (25.34 mmol) of the compound from Example 88A, dissolved in 150 ml of tetrahydrofuran, were added dropwise to 76.0 ml (76.0 mmol) of a 1N solution of diisobutylaluminum hydride in dichloromethane in 250 ml of tetrahydrofuran, and the reaction mixture was stirred at room temperature for 3 h. After addition of 1N hydrochloric acid, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were washed with saturated aqueous sodium chloride solution. Drying over sodium sulfate and filtration was followed by removal of the solvents in a rotary evaporator. The crude product was purified by flash chromatography on silica gel (mobile phase: dichloromethane/methanol gradient) to result in 5.55 g (91% purity, 85% of theory) of the title compound.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialDrying over sodium sulfate and filtration
  5. customwas followed by removal of the solvents in a rotary evaporator
  6. customThe crude product was purified by flash chromatography on silica gel (mobile phase: dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-b7683b66a4324227b41d0084db19eee5
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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