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

HRID 982061노트

반응식

HRID 982061 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96df92fa05884ad1b7e394c29a1945b1
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994494

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