Hydrochloric Acid → HCID 57452649, compound

HRID 546849Notes

Reaction equation

HRID 546849 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([C:17]([C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([CH3:46])[CH:40]=1)([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:28]([OH:37])([C:33]([F:36])([F:35])[F:34])[C:29]([F:32])([F:31])[F:30])=[C:22]([CH3:38])[CH:21]=1)[CH2:18][CH3:19])[CH3:16].Cl>O1CCCC1>[CH2:15]([C:17]([C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([CH3:46])[CH:40]=1)([C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([OH:37])([C:33]([F:34])([F:35])[F:36])[C:29]([F:32])([F:31])[F:30])=[C:22]([CH3:38])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 57433012HCID 57433012, compound

Product 1

HCID 57452649HCID 57452649, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium bis(2-methoxyethoxy)aluminum hydride (65 wt % solution in toluene, 17 mL, 56.74 mmol) was added to a solution of 4-{1-ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2-methyl-phenol (Example 25-(1); 8.67 g, 18.91 mmol) in tetrahydrofuran (100 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for one hour. The reaction mixture was then poured into 1 N hydrochloric acid aqueous solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 and 4:1) to give the target product as a colorless oil (6.11 g, 70%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 and 4:1)

Sources & evidence

ORD record
ord-8238e49515f7447bbba958448d5fa7ca
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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