反応 #42221

反応方程式

sodium hydroxide

9-borabicyclo[3.3.1]nonane

2-allyl-4-chloro-6-methoxyphenyl trifluoromethanesulfonate

potassium phosphate

hydrogen peroxide

→

6-chloro-4-methoxyindane

収率 68.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度the reaction mixture was heated
2. 2
   温度at reflux for 20 h
3. 3
   その他The solvent was removed in vacuo
4. 4
   その他to provide a crude oil
5. 5
   その他Purification by flash column chromatography (silica, hexanes)

実験手順

To 9-borabicyclo[3.3.1]nonane (130 mL, 0.5 M in tetrahydrofuran) cooled to 0° C. was added 2-allyl-4-chloro-6-methoxyphenyl trifluoromethanesulfonate (16.5 g, 0.050 mol) in tetrahydrofuran (100 mL), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (1.5 g, 1.84 mmol), and potassium phosphate (16.0 g, 0.075 mol) and the reaction mixture was heated at reflux for 20 h. The reaction mixture was allowed to cool to room temperature and aqueous sodium hydroxide (2.5 N, 30 mL) was added followed by hydrogen peroxide (30 wt. %, 25 mL) and stirring was continued for 1 h. The solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, hexanes) provided 6.2 g (68%) of 6-chloro-4-methoxyindane as a white solid. mp 38-40° C.; Anal. calcd. for C10H11ClO: C, 65.76; H, 6.07. Found: C, 66.08; H, 6.11.

出典