1-Piperidinecarboxaldehyde → HCID 22058586, compound

HRID 1828806Notes

Reaction equation

HRID 1828806 reaction equation
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

Participants

6

Reactant 4

HCID 174291-PiperidinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 22058631HCID 22058631, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 22058586HCID 22058586, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d9954cbc460f4d3fbbc43cc8b110e66c
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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