反応 #68812

反応方程式

tert-Butyl bromoacetate

4-hydroxybenzaldehyde

K2CO3

NaI

→

solid

収率 92.3%

4-(tert-Butoxycarbonylmethoxy)benzaldehyde

収率 92.3%

溶媒

CH2Cl2

Water

acetonitrile

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   その他the phases were separated
3. 3
   抽出The aqueous layer was extracted with CH2Cl2
4. 4
   洗浄The combined organic phase was washed with water
5. 5
   乾燥The organic layer was dried (Na2SO4)
6. 6
   その他Evaporation of the solvent and chromatography of the oily residue [silica, ethyl acetate/hexanes (3:7)]

実験手順

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.

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