Sodium hydride → Benzyl methyl 2-[3-[(4-methoxy)tetrahydropyran-4-yl]phenylmethyl]malonate

HRID 1839553ノート

反応式

HRID 1839553 の反応式
[C:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[CH3:18][O:19][C:20]1([C:26]2[CH:27]=[C:28]([CH2:32]Br)[CH:29]=[CH:30][CH:31]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CC(N(C)C)=O>[CH3:18][O:19][C:20]1([C:26]2[CH:27]=[C:28]([CH2:32][CH:2]([C:3]([O:5][CH3:6])=[O:4])[C:1]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:7])[CH:29]=[CH:30][CH:31]=2)[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5721351-Benzyl 3-methyl propanedioateHCID 102659323-[(4-Methoxy)tetrahydropyran-4-yl)-alpha-bromotoluene

生成物 1

HCID 53824197Benzyl methyl 2-[3-[(4-methoxy)tetrahydropyran-4-yl]phenylmethyl]malonate収率 53%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒3 回

反応条件

温度
5 °C

実験手順

A solution of benzyl methyl malonate (0.88 g, 4.22 mmol) in 3 mL of anhydrous DMA was added to a suspension of sodium hydride (0.11 g, 4.45 mmol) in 2 mL of anhydrous DMA at 5° C., and the reaction mixture was stirred for 40 min at 5° C. Then 3-[(4-methoxy)tetrahydropyran-4-yl]-α-bromotoluene [prepared as described in U.S. Pat. No. 5,424,320] (1.21 g, 4.24 mmol) was dissolved in 6 mL of anhydrous DMA and added to this solution. The reaction mixture was stirred for 2 h at 5° C., and for 18 h at room temperature. The reaction mixture was quenched with water (100 mL). The aqueous solution was extracted with ethyl acetate (3×70 mL). The combined organic extracts were washed with brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The concentrated residue was purified by flash column chromatography on silica gel, eluting with 20% ethyl acetate in hexane, to give 0.93 g (53%) of benzyl methyl 2-[3-[(4-methoxy) tetrahydropyran-4-yl]phenylmethyl]malonate as a clear oil: HRMS: calcd for C24H28O6 413.1964, found 413.1952.

後処理

  1. additionadded to this solution
  2. stirringThe reaction mixture was stirred for 2 h at 5° C.
  3. waitfor 18 h at room temperature
  4. customThe reaction mixture was quenched with water (100 mL)
  5. extractionThe aqueous solution was extracted with ethyl acetate (3×70 mL)
  6. washThe combined organic extracts were washed with brine (1×100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrated residue was purified by flash column chromatography on silica gel
  11. washeluting with 20% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-05bc8537b0454750a09dc166a529ae63
出典データセット
uspto-grants-2004_01
特許番号
US06677364B2

反応ノート

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