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Ethyl 2-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionate → 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionaldehyde

HRID 1274876
ノート
印刷プレビュー

反応式

HRID 1274876 の反応式
[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:15])([CH3:14])[C:9](OCC)=[O:10])[C:4](=[O:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.CCOCC.[Cl-].[Na+].O>[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:14])([CH3:15])[CH:9]=[O:10])[C:4](=[O:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 10968683Ethyl 2-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 221182842-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionaldehyde収率 61.2%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran
溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-40 °C

実験手順

A solution of ethyl 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (43 g) in tetrahydrofuran was added to lithium aluminium hydride (220 ml of a 1M solution in ether) with stirring at -40° C. After 1 hour the solution was cooled to -70° C., diluted with ether, and treated with brine via dropwise addition, initially at -70° C. and then at -30° C. After warning to room temperature the organic layer was dried (magnesium sulphate), evaporated and the residue purified by dry column chromatography on silica gel eluting with dichloromethane to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionaldehyde as a cream solid (22.5 g), NMR 1.35(s,6H), 1.95(s,3H), 5.25(s,2H), 7.22-7.38(m,5H), 9.42(s,1H).

後処理

  1. temperatureAfter 1 hour the solution was cooled to -70° C.
  2. customat -30° C
  3. customAfter warning to room temperature
  4. dry with materialwas dried (magnesium sulphate)
  5. customevaporated
  6. customthe residue purified
  7. dry with materialby dry column chromatography on silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-45e166af6d364581ad0e1ed6a164f470
出典データセット
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06159902

反応ノート

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