Water → HCID 69425060, compound

HRID 1593360Notes

Reaction equation

HRID 1593360 reaction equation
[CH2:1]([O:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[C:11]([F:22])[CH:12]=[C:13]([CH2:19][CH2:20][CH3:21])[CH:14]=3)[C:9](=O)[C:8]=2[C:7]=1[F:24])[CH2:2][CH2:3][CH3:4].C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[CH2:1]([O:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[C:11]([F:22])[CH:12]=[C:13]([CH2:19][CH2:20][CH3:21])[CH:14]=3)[CH2:9][C:8]=2[C:7]=1[F:24])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 694252382-Butoxy-1,8-difluoro-6-propyl-9H-fluoren-9-one

Product 1

HCID 69425060HCID 69425060, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Under exclusion of moisture, 3.8 g of 2-butyloxy-1,8-difluoro-6-propylfluoren-9-one (example 1) are dissolved in 50 ml of trifluoroacetic acid, and 4.6 ml of triethylsilane are added dropwise slowly at a temperature of 5-20° C. with gentle cooling. The mixture is subsequently stirred at room temperature for 1 h and then at 40-70° C. for 4 h. After cooling, the reaction mixture is added to water and extracted with dichloromethane. The combined org. phases are washed with water and 5% sodium hydrogencarbonate solution and dried over sodium sulfate. After the solvent has been removed in vacuo, the yellow residue is purified chromatographically on silica gel using 8:2 heptane/dichloromethane as eluent. After the solvent had been removed in vacuo, the product-containing fractions were recrystallized from heptane. 1.2 g of 2-butyloxy-1,8-difluoro-6-propylfluorene were obtained.

Workup

  1. waitat 40-70° C. for 4 h
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane
  4. washphases are washed with water and 5% sodium hydrogencarbonate solution
  5. dry with materialdried over sodium sulfate
  6. customAfter the solvent has been removed in vacuo
  7. customthe yellow residue is purified chromatographically on silica gel using 8:2 heptane/dichloromethane as eluent
  8. customAfter the solvent had been removed in vacuo
  9. customthe product-containing fractions were recrystallized from heptane

Sources & evidence

ORD record
ord-f1adff05903e4bdea2e76c0f195279f3
Source dataset
uspto-grants-2007_11
Patent number
US07297378B2

Reaction notes

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