Aluminium lithium hydride → (1-Formyl-2-naphthalen-2-ylethyl)carbamic acid tert-butyl ester

HRID 8535ノート

反応式

HRID 8535 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:20](=[O:25])NCOC)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([CH:20]=[O:25])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 69629212[1-(Methoxymethylcarbamoyl)-2-naphthalen-2-ylethyl]carbamic acid tert-butyl ester

生成物 1

HCID 20806433(1-Formyl-2-naphthalen-2-ylethyl)carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-55 °C

実験手順

To a solution of [1-(methoxymethylcarbamoyl)-2-naphthalen-2-ylethyl]carbamic acid tert-butyl ester, 67, (5.0 g, 13.4 mmol) in THF (40 mL) at −30° C. to −25° C. is added LAH (16.7 mL of a 1M solution in THF) over about 10 minutes and the reaction is then cooled to −55° C. and the stirring is continued for 3 hours. After cooling to −60° C., the reaction is quenched by the addition of citric acid in methanol (1:1 by weight). During quenching the temperature is maintained at about −45° C. The mixture is then allowed to warm to room temperature and partitioned between EtOAc and water and the water phase extracted again with EtOAc. The organic phases are combined and washed with sat NaCl, dried and concentrated in vacuo to afford the crude aldehyde as a white solid which is used without further purification.

後処理

  1. temperatureAfter cooling to −60° C.
  2. customthe reaction is quenched by the addition of citric acid in methanol (1:1 by weight)
  3. customDuring quenching the temperature
  4. temperatureis maintained at about −45° C
  5. temperatureto warm to room temperature
  6. custompartitioned between EtOAc and water
  7. extractionthe water phase extracted again with EtOAc
  8. washwashed with sat NaCl
  9. customdried
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3bcc3ad5af944641a39f0ca173a215de
出典データセット
uspto-grants-2006_08
特許番号
US07087759B2

反応ノート

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