反応 #459692

反応方程式

phthalimide

1-chloro-4-(2-tetrahydropyranyloxy)nonane

→

N-[4-(2-tetrahydropyranyloxy)nonyl]phthalimide

収率 45.0%

溶媒

dimethyl formamide

反応条件

後処理

1. 1
   洗浄Sodium hydride (53%) (1.5 g. excess) is washed with benzene three times by decantation
2. 2
   workup.ADDITIONdimethyl formamide (100 ml.) is added
3. 3
   その他the temperature below 35° C
4. 4
   その他A clear solution is obtained and to it
5. 5
   濃縮The reaction is then concentrated to one-half its volume in vacuo
6. 6
   workup.ADDITIONpoured into ice water (200 ml.)
7. 7
   抽出extracted with ether (2 × 150 ml.)
8. 8
   洗浄The ether is washed with 5% sodium hydroxide (2 × 50 ml.), saturated sodium chloride solution (2 × 50 ml.)
9. 9
   乾燥dried over sodium sulfate
10. 10
    その他Evaporation of the ether
11. 11
    その他affords 4.5 g

実験手順

Sodium hydride (53%) (1.5 g. excess) is washed with benzene three times by decantation, then dimethyl formamide (100 ml.) is added. To this stirred suspension is added a solution of phthalimide (4.3 g., 0.03 mole) in dimethyl formamide (50 ml.) at such a rate as to keep the temperature below 35° C. A clear solution is obtained and to it is added 1-chloro-4-(2-tetrahydropyranyloxy)nonane (7.8 g. 0.03 mole) and the resulting solution is stirred and heated at 95° C. for 20 hours. The reaction is then concentrated to one-half its volume in vacuo, poured into ice water (200 ml.) and extracted with ether (2 × 150 ml.). The ether is washed with 5% sodium hydroxide (2 × 50 ml.), saturated sodium chloride solution (2 × 50 ml.), then dried over sodium sulfate. Evaporation of the ether affords 4.5 g. (45% yield) of N-[4-(2-tetrahydropyranyloxy)nonyl]phthalimide melting 59°- 61° C. After crystallization from cyclohexane the product melts at 62°-63° C. Anal. Calcd. for C22H31NO4 : C, 70.75; H, 8.36; N, 3.75 Found: C, 71.03; H, 8.28; N, 3.81

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