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

HRID 8535노트

반응식

HRID 8535 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-55 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3bcc3ad5af944641a39f0ca173a215de
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087759B2

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