1-Piperidinecarboxaldehyde → HCID 22058586、化合物

HRID 1828806ノート

反応式

HRID 1828806 の反応式
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

参加物

6

反応物 4

HCID 174291-PiperidinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 22058631HCID 22058631、化合物HCID 178418244HCID 178418244、化合物

生成物 1

HCID 22058586HCID 22058586、化合物収率 42.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d9954cbc460f4d3fbbc43cc8b110e66c
出典データセット
uspto-grants-2006_06
特許番号
US07060721B1

反応ノート

読み込み中…