Hydrochloric Acid → HCID 22223131, compound

HRID 1744747Notes

Reaction equation

HRID 1744747 reaction equation
[CH2:1]([O:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[C:11]([F:19])[CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]=2[C:7]=1[F:20])[CH2:2][CH2:3][CH3:4].C([Li])CCC.CC(C)([O-])C.[K+].[CH:32](=[O:35])[CH2:33][CH3:34].Cl>O>[CH2:1]([O:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[C:11]([F:19])[C:12]([CH:32]([OH:35])[CH2:33][CH3:34])=[CH:13][CH:14]=3)[CH2:9][C:8]=2[C:7]=1[F:20])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 527PropanalHCID 12084324HCID 12084324, compoundHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

Product 1

HCID 22223131HCID 22223131, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The metallation of 23 mmol of 2-butoxy-1,8-difluorofluorene with 25 mmol of n-butyllithium (1.6 M solution in hexane) and 25 mmol of potassium tert-butoxide is effected in a similar manner to the procedure described in Example 1. 28 mmol mmol of propionaldehyde are subsequently added dropwise at ≦−70° C. and the mixture is allowed to thaw gradually. The reaction mixture is admixed at −10° C. with 50 ml of water and acidified to pH I using concentrated hydrochloric acid. The mixture is extracted using tert-butyl methyl ether, the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate, and the solvent is removed under reduced pressure. Chromatography on silica gel using dichloromethane as eluent provides 2-butoxy-1,8-difluoro-7-(1-hydroxypropyl)fluorene.

Workup

  1. extractionThe mixture is extracted
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-41741fdffb5441139b15e91beb4cdab8
Source dataset
uspto-grants-2006_03
Patent number
US07018685B2

Reaction notes

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