反应 #554667

反应方程式

Sodium hydride

3-methyl-1,4-oxazepan-5-one

Benzyl bromide

→

4-benzyl-3-methyl-1,4-oxazepan-5-one

溶剂

DMF

反应条件

后处理

1. 1
   workup.STIRRINGstirred for 20 h
2. 2
   其他The reaction mixture was partitioned between brine (100 mL) and ethyl acetate (2×100 mL)
3. 3
   干燥the combined organic layers were dried over sodium sulfate
4. 4
   浓缩concentrated
5. 5
   其他The residue was purified by flash column chromatography (20% EtOAc in hexanes initially

实验过程

Sodium hydride (95%, 553 mg, 21.9 mmol, 1.15 equiv) was added to a solution of 3-methyl-1,4-oxazepan-5-one (4-2, 2.46 g, 19.0 mmol, 1 equiv) in DMF (40 mL) at 0° C. and the resulting mixture was stirred for 20 min. Benzyl bromide (2.49 mL, 20.9 mmol, 1.10 equiv) was added and the mixture was warmed to 23° C. and stirred for 20 h. The reaction mixture was partitioned between brine (100 mL) and ethyl acetate (2×100 mL), and the combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (20% EtOAc in hexanes initially, grading to 100% EtOAc) to give 4-benzyl-3-methyl-1,4-oxazepan-5-one (4-3) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.36-7.25 (m, 5H), 5.05 (d, 1H,J=14.6 Hz), 4.17 (d, 1H,J=14.6 Hz), 4.00 (ddd, 1H,J=12.5, 6.1, 3.3 Hz), 3.80 (dd, 1H,J=12.8, 4.0 Hz), 3.56 (dd, 1H,J=12.5 Hz), 3.42 (d, 1H,J=12.8 Hz), 3.31 (m, 1H), 3.02 (ddd, 1H,J=15.0, 11.9, 3.4 Hz), 2.75 (ddd, 1H,J=16.2, 4.9, 1.2 Hz), 1.31 (d, 3H,J=7.3 Hz). LRMS m/z (M+H) 220.3 found, 220.1 required.

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