Dimethylformamide → 3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde
Reaction equation
[C:1]([Si:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CN(C)CCN(C)CCN(C)C.CN(C)[CH:37]=[O:38]>C1COCC1>[Si:5]([O:8][CH2:9][CH2:10][C:11]1[C:12]([F:17])=[C:13]([CH:14]=[CH:15][CH:16]=1)[CH:37]=[O:38])([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:6])[CH3:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
tert-Butyl(2-fluorophenethoxy)dimethylsilane (example 78, step a) (5.00 g) was added over 5 minutes to a stirred solution of sec-butyllithium (1.4 molar solution in cyclohexane, 14.0 mL) and N1-(2-(dimethylamino)ethyl)-N1,N2,N2-trimethylethane-1,2-diamine (4.10 mL) in THF (25 mL) cooled to −78° C. After 2 h, N,N-dimethylformamide (10.06 g) was added, the reaction mixture was stirred at −78° C. for 1 h, and then the cooling bath was removed. After a further 0.5 h, the reaction was quenched with water. Ethyl acetate (300 mL) was added and the reaction mixture washed with water (3×150 mL), 2M HCl (2×50 mL), water (2×50 mL), brine then dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as an oil. Yield 5.3 g.
Workup
- customthe cooling bath was removed
- waitAfter a further 0.5 h
- customthe reaction was quenched with water
- additionEthyl acetate (300 mL) was added
- washthe reaction mixture washed with water (3×150 mL), 2M HCl (2×50 mL), water (2×50 mL), brine
- dry with materialthen dried over sodium sulphate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-c73e457a753c4c1f90c81234264b5cea
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148373B2
Reaction notes
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