Methyl acetoacetate → methyl (E)-7-[3-(4-fluorophenyl)bicyclo[3.2.1]oct-2-en-2-yl]-5-hydroxy-3-oxohept-6-enoate

HRID 982061ノート

反応式

HRID 982061 の反応式
[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].C([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:29][CH:28]3[CH2:30][CH:25]([CH2:26][CH2:27]3)[C:24]=2[CH:31]=[CH:32][CH:33]=[O:34])=[CH:19][CH:18]=1>C1COCC1.CCCCC>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH2:29][CH:28]3[CH2:30][CH:25]([CH2:26][CH2:27]3)[C:24]=2/[CH:31]=[CH:32]/[CH:33]([OH:34])[CH2:7][C:5](=[O:6])[CH2:4][C:3]([O:9][CH3:10])=[O:8])=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 537275483-[3-(4-Fluorophenyl)bicyclo[3.2.1]oct-2-en-2-yl]-propenalHCID 178418339Butyllithium

生成物 1

HCID 14677528methyl (E)-7-[3-(4-fluorophenyl)bicyclo[3.2.1]oct-2-en-2-yl]-5-hydroxy-3-oxohept-6-enoate

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a 0°-5° C. suspension of pentane-washed sodium hydride (0.43 g, 10.6 mmoles) in 10 ml anhydrous THF was added dropwise methyl acetoacetate. The solution was stirred for 30 minutes and n-butyl lithium (5.8 ml of a 1.6M solution in hexanes, 9.31 mmoles) was added dropwise. The solution was stirred for 20 minutes and a solution of 3-[3-(4-fluorophenyl)bicyclo [3.2.1]oct-2-en-2-yl]propenal (2.50 g, 9.75 mmoles) in 15 ml anhydrous THF was added. The resulting solution was stirred for 60 minutes and quenched with ether and aqueous HCl. The organic layer was washed with water and brine and dried (MgSO4). Removal of the volatiles in vacuo provided 3.3 g of the solid product which was used without further purification.

後処理

  1. stirringThe solution was stirred for 20 minutes
  2. stirringThe resulting solution was stirred for 60 minutes
  3. customquenched with ether and aqueous HCl
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customRemoval of the volatiles in vacuo

出典と根拠

ORDレコード
ord-96df92fa05884ad1b7e394c29a1945b1
出典データセット
uspto-grants-1991_02
特許番号
US04994494

反応ノート

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