Ammonium Chloride → 1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(2,6-dichlorophenyl)ethanol

HRID 1489736Notes

Reaction equation

HRID 1489736 reaction equation
C([Li])CCC.[CH:6]1([O:11][C:12]2[CH:13]=[C:14](Br)[CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1[CH2:29][CH:30]=[O:31].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH:6]1([O:11][C:12]2[CH:13]=[C:14]([CH:30]([OH:31])[CH2:29][C:23]3[C:22]([Cl:21])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:28])[CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzeneHCID 122635642-(2,6-Dichlorophenyl)acetaldehydeHCID 178418339Butyllithium

Product 1

HCID 211878701-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(2,6-dichlorophenyl)ethanolYield 33.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of butyl lithium in hexane (5.1 mL; 2.5M) is treated with a solution of 3-cyclopentyloxy-4-methoxyphenyl bromide (3.45 g) in dry tetrahydrofuran (30 mL) at -70° C. and the solution is then stirred at -70° C. for 1 hour. It is then treated dropwise with 2,6-dichlorophenylacetaldehyde (2.4 g), while keeping the temperature below -60° C. When the addition is complete the temperature is allowed to rise to room temperature and the solution is stirred for a further 2 hours. The reaction mixture is treated with aqueous ammonium chloride solution (50 mL) and the solution is extracted with diethyl ether (2×200 mL). The combined extracts are dried and concentrated, to give a yellow oil, which is subjected to flash chromatography, eluting with a mixture of diethyl ether and pentane (1:8 v/v), to give 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(2,6-dichlorophenyl)ethanol (1.6 g),in the form of a white solid, m.p. 87°-89° C.

Workup

  1. customthe temperature below -60° C
  2. additionWhen the addition
  3. customto rise to room temperature
  4. stirringthe solution is stirred for a further 2 hours
  5. extractionthe solution is extracted with diethyl ether (2×200 mL)
  6. customThe combined extracts are dried
  7. concentrationconcentrated
  8. customto give a yellow oil, which
  9. washeluting with a mixture of diethyl ether and pentane (1:8 v/v)

Sources & evidence

ORD record
ord-4a3789ebaa034bb8ba99ebd70526ff88
Source dataset
uspto-grants-1997_10
Patent number
US05679696

Reaction notes

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