تفاعل #68812

معادلة التفاعل

tert-Butyl bromoacetate

4-hydroxybenzaldehyde

K2CO3

NaI

→

solid

المردود 92.3%

4-(tert-Butoxycarbonylmethoxy)benzaldehyde

المردود 92.3%

المذيبات

CH2Cl2

Water

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   أخرىthe phases were separated
3. 3
   استخلاصThe aqueous layer was extracted with CH2Cl2
4. 4
   غسيلThe combined organic phase was washed with water
5. 5
   تجفيفThe organic layer was dried (Na2SO4)
6. 6
   أخرىEvaporation of the solvent and chromatography of the oily residue [silica, ethyl acetate/hexanes (3:7)]

الإجراء التجريبي

A solution of 4-hydroxybenzaldehyde (2.44 g, 20.0 mmol) in dry acetonitrile (8.0 mL) was treated with powdered, dried K2CO3 (3.04 g, 22.0 mmol) and NaI (304 mg, 2.00 mmol). The mixture was refluxed under argon for 30 min. tert-Butyl bromoacetate (1.48 mL, 1.95 g, 10.0 mmol) was added dropwise, and the reflux was continued for 12 h. Water and CH2Cl2 were added and the phases were separated. The aqueous layer was extracted with CH2Cl2. The combined organic phase was washed with water. The organic layer was dried (Na2SO4). Evaporation of the solvent and chromatography of the oily residue [silica, ethyl acetate/hexanes (3:7)] afforded a white, crystalline solid (2.18 g, 92%): mp 56-57° C.; IR (film, νmax cm−1) 1762, 1752, 1685, 1600; 1H NMR δ 1.48 (s, 9H), 4.60 (s, 2H), 6.99 (d, J=8.7 Hz, 2H), 7.84 (d, J=8.7 Hz, 2H), 9.89 (s, 1H); 13C NMR δ 28.25, 65.76, 83.17, 115.08, 130.82, 132.18, 163.00, 167.37, 190.98; EI-MS 105/107, 135, 193/194, 236/237; FAB-MS obsd 237.1120, calcd 237.1127 [(M+H)+, M=C13H16O4]; Anal. Calcd C, 66.09; H, 6.83. Found C, 66.06; H, 6.82.

المصدر