Dimethylformamide → 3-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

HRID 1438157Notes

Reaction equation

HRID 1438157 reaction equation
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=1[F:17])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.CN([CH:26]=[O:27])C>C1COCC1.CN(C)CCN(C)CCN(C)C.CCOC(C)=O>[Si:5]([O:8][C:9]1[C:10]([F:17])=[C:11]([CH:12]=[C:13]([CH2:15][CH3:16])[CH:14]=1)[CH:26]=[O:27])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 59838026tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 598380723-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehydeYield 89%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 18196PentamethyldiethylenetriamineSolvent

Procedure

To 118B (625 mg, 2.46 mmol) in THF (10 mL) and N,N,N′,N″,N″-pentamethyldiethylenetriamine (0.77 mL) was added n-BuLi (1.6M in hexane, 1.77 mL) at −78° C. After stiiring for 45 min at −35° C., DMF (0.94 mL) was added at at −78° C. and the reaction was slowly warmed up to rt. The mixture was stirred at rt for 1 h, diluted with EtOAc. The organic extracts were washed with saturated NaHCO3, brine and dried. The crude product was purified by column chromatography to give 118C (615 mg, 89% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 0.21 (s, 6H) 1.01 (s, 9H) 1.21 (t, J=7.47 Hz, 3H) 2.59 (q, J=7.47 Hz, 2H) 6.99 (dd, J=7.91, 2.20 Hz, 1H) 7.21-7.27 (m, 1H) 10.30 (s, 1H).

Workup

  1. washThe organic extracts were washed with saturated NaHCO3, brine
  2. customdried
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-9016d048280b4e30965a0f79c9171c05
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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