Crotonaldehyde → HCID 53919901, compound
Reaction equation
[CH:1](=O)/[CH:2]=[CH:3]/[CH3:4].[Si:6]([O:13][NH2:14])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>C(Cl)Cl>[Si:6]([O:13][N:14]=[CH:1][CH:2]=[CH:3][CH3:4])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
The procedure followed was that described by Behforouz et al., J. Org. Chem. 58:7089-7091 (1993). In a 50 mL round bottom flask dry, 4 Å molecular sieves (Fisher, 3.4 g) were added to dry CH2Cl2 (distilled from CaH2, 10 mL) and cooled to 5° C. with an ice bath. Freshly distilled crotonaldehyde (Matheson Coleman & Bell, 0.725 mL, 0.618 g, 8.84 mmol) was added. A solution of O-(tert-butyldimethylsilyl)hydroxylamine (Aldrich, used without purification, 1.0 g, 6.80 mmol) in dry CH2Cl2 (distilled from CaH2, 3 mL) was added dropwise over a period of 5 min. The ice bath was removed and the mixture was stirred at rt under N2 for 18 h. The sieves were removed by filtration and the CH2Cl2 was evaporated to dryness (roto-vap). Column chromatography on silica gel with CHCl3 as eluent afforded 1-(tert-butyldimethylsilyloxy)-1-aza-1,3-pentadiene as a colorless light oil (1.2 g, 88%, interpretation of the 1H NMR showed a 1:1 anti/syn mixture): 1H NMR (CDCl3) δ (anti) 0.18 (s, 6H), 0.95 (s, 9H), 1.85-1.88 (m, 3H), 5.93-6.23 (m, 1H), 6.7-6.9 (m, 1H), 7.18 (d, 1H); (syn) 0.18 (s, 6H), 0.95 (s, 9H), 1.85-1.88 (m, 3H), 5.93-6.15 (m, 2H), 7.81 (d, 1H).
Workup
- customIn a 50 mL round bottom flask dry
- addition4 Å molecular sieves (Fisher, 3.4 g) were added to dry CH2Cl2 (distilled from CaH2, 10 mL)
- customThe ice bath was removed
- customThe sieves were removed by filtration
- customthe CH2Cl2 was evaporated to dryness (roto-vap)
Sources & evidence
- ORD record
- ord-e0f89f7f88dc47ed964acea214b61163
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05708168
Reaction notes
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