Chlorotrimethylsilane → 5-(Trimethylsilyl)furan-3-carbaldehyde

HRID 1492929Notes

Reaction equation

HRID 1492929 reaction equation
C([Li])CCC.N1CCOCC1.Br[C:13]1[O:17][CH:16]=[C:15]([CH:18]=[O:19])[CH:14]=1.Cl[Si:21]([CH3:24])([CH3:23])[CH3:22]>CCCCCC.O1CCCC1>[CH3:22][Si:21]([CH3:24])([CH3:23])[C:13]1[O:17][CH:16]=[C:15]([CH:18]=[O:19])[CH:14]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8083MorpholineHCID 150370565-Bromofuran-3-carbaldehydeHCID 178418339Butyllithium2×

Product 1

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

n-Butyl lithium (a 1.6M solution in hexane; 31.0 ml, 49.7 mmol) was added dropwise to a solution of morpholine (4.33 ml, 49.7 mmol; freshly distilled from barium oxide) in tetrahydrofuran at -78° under argon. After 15 minutes, a solution of 5-bromo-3-furaldehyde (7.5 g, 49.7 mmol) in tetrahydrofuran (THF) was added dropwise. Stirring was continued for 30 min. and n-butyl lithium (a 1.6M solution in hexane; 46.6 ml, 74.5 mmol) was added dropwise. After 1 hour at -78°, chlorotrimethylsilane (18.9 ml, 149 mmol) was added and stirring continued while the cooling bath attained room temperature. The reaction mixture was quenched with 10% hydrochloric acid and the phases were separated. The aqueous phase was stirred, in the presence of ethyl ether (30 ml), with 10% hydrochloric acid at 0° C. for 1/2 hour. The organic phases were combined, washed (brine), dried (magnesium sulfate) and evaporated down. The residue was distilled under vacuum to give the title aldehyde as a colorless oil b.p. 48-50°/0.25 torr.

Workup

  1. distillationfreshly distilled from barium oxide) in tetrahydrofuran at -78° under argon
  2. waitwas continued for 30 min.
  3. addition46.6 ml, 74.5 mmol) was added dropwise
  4. waitAfter 1 hour at -78°
  5. stirringstirring
  6. customcontinued while the cooling bath attained room temperature
  7. customThe reaction mixture was quenched with 10% hydrochloric acid
  8. customthe phases were separated
  9. stirringThe aqueous phase was stirred, in the presence of ethyl ether (30 ml), with 10% hydrochloric acid at 0° C. for 1/2 hour
  10. washwashed (brine)
  11. dry with materialdried (magnesium sulfate)
  12. customevaporated down
  13. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-9c02c24eb6fc40ef8ccfc059d2b32d14
Source dataset
uspto-grants-1994_12
Patent number
US05376676

Reaction notes

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