1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 3-oxo-4-phenyl-2-(1-cyano-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-butyrate

HRID 6398

反応式

HRID 6398 の反応式
[O:1]=[C:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:15]([C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH:18]=1)#[N:16].C1CCN2C(=NCCC2)CC1>C(#N)C>[O:1]=[C:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:3]([CH:18]1[CH2:19][CH2:20][C:21]2[C:26](=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)[CH:17]1[C:15]#[N:16])[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2 回HCID 2760261Methyl 3-oxo-4-phenylbutanoateHCID 30144661-Naphthalenecarbonitrile, 3,4-dihydro-6-methoxy-2 回

生成物 1

HCID 19793281Methyl 3-oxo-4-phenyl-2-(1-cyano-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-butyrate収率 65%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Methyl 3-oxo-4-phenylbutyrate (29.33 g, 153 mmol) and 1-cyano-6-methoxy-3,4-dihydronaphthalene (25.7, 139 mmol), the product of Step 2 of Example 1, were dissolved in 25 mL of acetonitrile. DBU (1.5 mL) was added and the reaction mixture was stirred for 2 h at ambient temperature. A second aliquot of DBU (1.5 mL) was then added and stirring continued overnight. The reaction mixture was partitioned between diethyl ether and 1N aqueous hydrochloric acid solution (4:1) and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with 1N aqueous hydrochloric acid and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel eluted with hexane/ethyl acetate (6:1) to give 33.9 g (65% yield) of the title compound; MS DCl--NH3M/Z: 395 (M+NH4)+.

後処理

  1. stirringstirring continued overnight
  2. customThe reaction mixture was partitioned between diethyl ether and 1N aqueous hydrochloric acid solution (4:1)
  3. extractionthe aqueous layer was extracted with diethyl ether
  4. washThe combined organic layers were washed with 1N aqueous hydrochloric acid and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on silica gel
  9. washeluted with hexane/ethyl acetate (6:1)

出典と根拠

ORDレコード
ord-4f061f4471424f05a5f309faf9ef5632
出典データセット
uspto-grants-1993_09
特許番号
US05248677

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