1-Piperidinecarboxaldehyde → HCID 22058586, 화합물

HRID 1828806노트

반응식

HRID 1828806 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([Cl:27])[CH:3]=1.C([Li])CCC.CCCCCC.[CH:39](N1CCCCC1)=[O:40].[Cl-].[NH4+]>O1CCCC1>[O:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:39]=[O:40])=[CH:3][C:4]=1[Cl:27])[Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 174291-PiperidinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 22058631HCID 22058631, 화합물HCID 178418244HCID 178418244, 화합물

생성물 1

HCID 22058586HCID 22058586, 화합물수율 42.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
10 °C

실험 절차

To a solution of 4-bromo-1-((tert-butyldiphenylsiloxy)methyl)-2-chlorobenzene (8.65 g) in tetrahydrofuran (22 ml) was added 1-butyl lithium/hexane solution (1.54M, 13.5 ml) at −75° C. in a nitrogen atmosphere, and the mixture was stirred for 15 min. The reaction mixture was once heated to 10° C. and again cooled to −75° C. and 1-formyl piperidine (2.55 g) was added dropwise over 10 min. The reaction mixture was heated to room temperature over 3 hr. To the reaction mixture was added aqueous ammonium chloride solution and the resulting product was extracted twice with hexane. The organic layers were combined, washed successively with dil. hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was applied to silica gel column chromatography (hexane/ethyl acetate=40/1) to give 4-((tert-butyldiphenylsiloxy)methyl)-3-chlorobenzaldehyde (3.26 g) as a pale-yellow oil.

후처리

  1. temperatureagain cooled to −75° C.
  2. temperatureThe reaction mixture was heated to room temperature over 3 hr
  3. extractionthe resulting product was extracted twice with hexane
  4. washwashed successively with dil. hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-d9954cbc460f4d3fbbc43cc8b110e66c
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060721B1

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