反応 #50473

反応方程式

HCl

6-fluoro-3,4-dihydro-1(2H)-naphthlenone

dimethylcarbonate

sodium hydride

→

solid

収率 98.2%

methyl 6-fluoro-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate

収率 98.2%

溶媒

tetrahydrofuran

ether

tetrahydrofuran

Hexane

反応条件

後処理

1. 1
   workup.ADDITIONwas added in one portion
2. 2
   温度The solution was heated
3. 3
   温度to reflux
4. 4
   温度while maintaining
5. 5
   温度reflux
6. 6
   workup.ADDITIONAfter the addition
7. 7
   温度the reaction was refluxed for 1.5 hours
8. 8
   温度The reaction was then cooled in an ice bath
9. 9
   その他the aqueous phase was separated
10. 10
    抽出extracted twice with ether
11. 11
    乾燥The combined organic phases were dried (MgSO4)
12. 12
    濃縮concentrated

実験手順

Hexane washed sodium hydride (3.5 g of 60%, 88 mmole) was covered with 75 ml of tetrahydrofuran and 5.4 ml (64 mmole) of dimethylcarbonate was added in one portion. The solution was heated to reflux and 6-fluoro-3,4-dihydro-1(2H)-naphthlenone (7.2 g, 44 mmole) in 25 ml of tetrahydrofuran was added dropwise while maintaining reflux. After the addition was complete, the reaction was refluxed for 1.5 hours. The reaction was then cooled in an ice bath and 10% aqueous HCl solution was carefully added. The solution was diluted with ether and the aqueous phase was separated and extracted twice with ether. The combined organic phases were dried (MgSO4) and concentrated. The crude product was a pale yellow solid (9.6 g, 98% yield). 1H NMR (CDCl3) δ: 7.99 (1H, dd, J=6,8 Hz), 6.95 (2H, m) 3.83 (3H, s), 3.82 (1H, m), 2.81 (2H, m), 2.58 (2H, m). NMR complicated by signals from enol tautomer.

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