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

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.

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

ORD record

ord-86c2499c10fe4422a0a1f2a0b41b0486

Source dataset

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05045564