P-Chloroacetophenone → HCID 86722006、化合物

HRID 1398042ノート

反応式

HRID 1398042 の反応式
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([C:8](Cl)=[O:9])[CH2:5][CH2:4][O:3]1.CCOCC.[Mg+2].[Br-].[Br-].[CH3:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[O:22].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23](/[C:21](/[OH:22])=[CH:20]/[C:8]([CH:6]2[CH2:5][CH2:4][O:3][C:2]([CH3:11])([CH3:1])[CH2:7]2)=[O:9])=[CH:24][CH:25]=1

参加物

6

反応物 4

HCID 7467P-ChloroacetophenoneHCID 81531DiisopropylethylamineHCID 9903262Magnesium bromide diethyl etherateHCID 122964132,2-dimethyltetrahydro-2H-pyran-4-carbonyl chloride

生成物 1

HCID 86722006HCID 86722006、化合物収率 58.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 2,2-dimethyltetrahydro-2H-pyran-4-carbonyl chloride (0.55 g, 3.14 mmol), magnesium bromide diethyl etherate (1.35 g, 5.23 mmol), and 4-chloroacetophenone (0.34 mL, 2.62 mmol) in 12 mL of DCM at RT was added dropwise DIEA (1.45 mL, 7.85 mmol). The mixture was stirred overnight and then diluted with 50 mL of DCM and washed with 1N HCl (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, concentrated, and the crude product was purified by silica gel chromatography (Thomson Scientific 25-g cartridge, 2-20% EtOAc/heptane in 10 column volumes) to give 0.45 g (58%) of the title compound as a light orange solid. The NMR of this compound shows that it exists in the enone form in CDCl3.

後処理

  1. washwashed with 1N HCl (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe crude product was purified by silica gel chromatography (Thomson Scientific 25-g cartridge, 2-20% EtOAc/heptane in 10 column volumes)

出典と根拠

ORDレコード
ord-2bc7bdd3851441c28a03dbcce7d8ca87
出典データセット
uspto-grants-2014_12
特許番号
US08901314B2

反応ノート

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