Dimethyl Carbonate → Methyl 7-cyclohexyl-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate

HRID 861867ノート

反応式

HRID 861867 の反応式
[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].[C:21](=O)([O:24]C)[O:22][CH3:23]>>[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH:13]([C:21]([O:22][CH3:23])=[O:24])[C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

4

反応物 3

HCID 12021Dimethyl CarbonateHCID 10942334Sodium MethoxideHCID 15324703HCID 15324703、化合物

生成物 1

HCID 19700499Methyl 7-cyclohexyl-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate収率 74%

実験手順

A mixture of 7-cyclohexyl-1-tetralone (9.4 g), sodium methoxide (8.9 g) and dimethyl carbonate (65 ml) was refluxed for 30 minutes in a nitrogen gas stream. After the reaction mixture was cooled, the resulting crystals were collected by filtration and suspended in ethyl acetate (250 ml), followed by addition of 6N HCl (50 ml). The organic layer was collected, while the aqueous layer was extracted with ethyl acetate. The extract was combined with the organic layer, successively washed with water and brine, and dried (MgSO4), after which the solvent was evaporated off, to yield methyl 7-cyclohexyl-1-tetralone-2-carboxylate (8.6 g, 74%) as an oil.

後処理

  1. temperaturewas refluxed for 30 minutes in a nitrogen gas stream
  2. temperatureAfter the reaction mixture was cooled
  3. filtrationthe resulting crystals were collected by filtration
  4. additionfollowed by addition of 6N HCl (50 ml)
  5. customThe organic layer was collected, while the aqueous layer
  6. extractionwas extracted with ethyl acetate
  7. washsuccessively washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customafter which the solvent was evaporated off

出典と根拠

ORDレコード
ord-ac582ceb4e8146d48ee8583c987008d4
出典データセット
uspto-grants-1998_02
特許番号
US05716944

反応ノート

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