Triethylsilane → HCID 18470227, compound

HRID 2228897Notes

Reaction equation

HRID 2228897 reaction equation
C([SiH](CC)CC)C.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=O>CCOCC>[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 12052Triethylsilane2×HCID 18470115HCID 18470115, compound

Product 1

HCID 18470227HCID 18470227, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylsilane (30.5 g, 260 mmol) was added dropwise to 8-bromo-1-(4-fluorophenyl)octan-1-one (230 ml, 105 mmol) over 20 min, with cooling to keep the temperature at ca 30° C. After 2 hours stirring, a further 3.1 g (27 mmol) triethylsilane was added, and reaction continued for an additional 2 hours. The mixture was poured into ice-water (200 ml) and ether (300 ml), then the organic layer was washed with aqueous sodium hydroxide. dried and evaporated, finally at 65° C./0.01 mm. The residue was filtered through silica gel, eluting with petroleum ether, then distilled, collecting the fraction at 122-140° C./0.5 mm (24.2 g). 1H-NMR (CDCl3) δ 1.2-1.7 (10H, m), 1.85 (2H, m), 2.57 (2H, t), 3.40 (2H, t), 6.9-7.05 (2H, m) and 7.05-7.2 (2H, m).

Workup

  1. temperaturewith cooling
  2. customat ca 30° C
  3. customreaction
  4. waitcontinued for an additional 2 hours
  5. washthe organic layer was washed with aqueous sodium hydroxide
  6. customdried
  7. customevaporated, finally at 65° C./0.01 mm
  8. filtrationThe residue was filtered through silica gel
  9. washeluting with petroleum ether
  10. distillationdistilled
  11. customcollecting the fraction at 122-140° C./0.5 mm (24.2 g)

Sources & evidence

ORD record
ord-539b6c0abb054b4fb60291226e768256
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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