Hexane → 6-(t-Butyl-diphenylsilyloxy)-1-(2,5-difluorophenyl)-1-hexanol

HRID 748752Notes

Reaction equation

HRID 748752 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[F:9].CCCCCC.C([Li])CCC.[Si:21]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH:44]=[O:45])([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C.C(OCC)C.O1CCCC1>[Si:21]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH:44]([C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[F:9])[OH:45])([C:34]([CH3:36])([CH3:37])[CH3:35])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 8058HexaneHCID 678622-Bromo-1,4-difluorobenzeneHCID 117924786-(t-butyldiphenylsilyloxy)hexanalHCID 178418339Butyllithium

Product 1

HCID 597508086-(t-Butyl-diphenylsilyloxy)-1-(2,5-difluorophenyl)-1-hexanolYield 88%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran (30 ml) solution of 1-bromo-2,5-difluorobenzene (0.956 ml, 8.46 mmol) was stirred at −78° C. To the reaction mixture was added a hexane solution (6.46 ml, 10.2 mmol) of n-butyl lithium. The reaction mixture was added to a tetrahydrofuran (20 ml) solution of 6-(t-butyldiphenylsilyloxy)hexanal (2.50 g, 7.05 mmol) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. After the temperature of the reaction mixture was elevated to room temperature, diethyl ether was added thereto. The mixture was washed with a saturated aqueous solution of ammonium chloride and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=9:1 eluate was concentrated under reduced pressure, whereby the title compound (2.92 g, 4.65 mmol, 88%) was obtained as a colorless oil.

Workup

  1. customwas elevated to room temperature
  2. washThe mixture was washed with a saturated aqueous solution of ammonium chloride
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe fraction obtained from the hexane

Sources & evidence

ORD record
ord-672c55347b894629ad905d35eafce500
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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