1-Tetralone → HCID 22038410, compound

HRID 1431967Notes

Reaction equation

HRID 1431967 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[C:13]1(=[O:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1.[Cl-].[NH4+]>CCCCCC.CCOCC>[N:10]1[CH:11]=[CH:12][C:7]([C:13]2([OH:23])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 107241-TetraloneHCID 142684-BromopyridineHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 22038410HCID 22038410, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

85 ml of a 1.5M solution of n-butyllithium in hexane are added, dropwise, to a solution of 20 g of 4-bromopyridine in 73 ml of ether, cooled to −78° C. Stirring is carried out for 30 minutes at that temperature, a solution of 1-tetralone in 73 ml of ether is then poured in and, at the end of the addition, the mixture is allowed to return to ambient temperature. After stirring overnight, a saturated aqueous solution of ammonium chloride is poured in. After separation, extraction with ether is carried out. The ethereal phases are combined and extracted with 1N hydrochloric acid. The combined acid phases are adjusted to pH=8 using 20% sodium hydroxide solution and extracted with dichloromethane. After drying, the expected product is isolated, which is purified by high-speed chromatography on silica (eluant: dichloromethane/methanol 95/5) to yield the expected product.

Workup

  1. additionat the end of the addition
  2. customto return to ambient temperature
  3. stirringAfter stirring overnight
  4. customAfter separation, extraction with ether
  5. extractionextracted with 1N hydrochloric acid
  6. extractionextracted with dichloromethane
  7. customAfter drying

Sources & evidence

ORD record
ord-9e19de76c80a426ca048d5faa8c01643
Source dataset
uspto-grants-2009_11
Patent number
US07612061B2

Reaction notes

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