Hydrochloric Acid → 2-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol

HRID 258263Notes

Reaction equation

HRID 258263 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CCCCCC.[Cl:19][C:20]1[CH:33]=[CH:32][C:23]([CH2:24][C:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH:26]=[O:27])=[CH:22][CH:21]=1.[Cl-].[NH4+].Cl>C(OCC)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][C:25]([CH2:28][CH3:29])([CH2:30][CH3:31])[CH:26]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[OH:27])=[CH:32][CH:33]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 122863-BromopyridineHCID 25517Ammonium ChlorideHCID 151008312-(4-Chlorobenzyl)-2-ethylbutanalHCID 178418339Butyllithium

Product 1

HCID 151008322-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of 15.8 g of 3-bromopyridine (0.10 mol) in 50 ml of diethyl ether is added dropwise to a mixture of 82 ml of a 1.6M n-butyllithium solution in n-hexane (0.13 mol) under a nitrogen atmosphere at -70° C. The mixture is stirred at -70° C. for 10 minutes and then a solution of 24.7 g of 2-(4-chlorobenzyl)-2-ethylbutanal (0.11 mol) in 50 ml of diethyl ether is added dropwise. After 1 h at -70° C., the mixture is allowed to warm slowly to room temperature and is hydrolyzed with saturated aqueous ammonium chloride solution. The mixture is acidified with dilute hydrochloric acid, and the aqueous phase is separated off and washed with ether and then adjusted to pH 10 to 11 with concentrated ammonia solution while cooling. It is extracted three times with dichloromethane, and the organic phase is dried over Na2SO4 and concentrated. The solid crude product is recrystallized from ethyl acetate/hexane (1:1). 19.2 g (63% of theory) of colorless crystals of melting point 128°-129° C.

Workup

  1. waitAfter 1 h at -70° C.
  2. temperatureto warm slowly to room temperature
  3. customthe aqueous phase is separated off
  4. washwashed with ether
  5. temperaturewhile cooling
  6. extractionIt is extracted three times with dichloromethane
  7. dry with materialthe organic phase is dried over Na2SO4
  8. concentrationconcentrated
  9. customThe solid crude product is recrystallized from ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-6059a885e0654250aeec936e14101a85
Source dataset
uspto-grants-1993_11
Patent number
US05266579

Reaction notes

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