1-Bromo-5-chloropentane → HCID 86181973, compound

HRID 2292499Notes

Reaction equation

HRID 2292499 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[Cl:10])=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][Cl:29].[O-]CC.[Na+]>C(O)C>[Cl:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[Cl:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 960701-Bromo-5-chloropentaneHCID 2723922Sodium ethoxideHCID 4553080Des-N,N-diethylethanaMine 4-HydroxycloMiphene

Product 1

HCID 86181973HCID 86181973, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Combine (E and Z)-1-[(4-hydroxy)phenyl]-1,2-diphenyl-2-chloro-ethylene (2.3 g, 7.5 mmol) and 5-bromo-1-chloropentane (2.78 g, 15.0 mmol) in ethanol (40 mL). Add a solution of sodium ethoxide in ethanol (11.12 mL, 0.67M, 7.5 mmol). Heat to reflux under an inert atmosphere. After 24 hours concentrate in vacuo. Chromatograph on silica gel eluting with 1/7 ethyl acetate/hexane. Concentration of the product containing fractions to give the title compound which is taken on to the next step without further purification.

Workup

  1. temperatureHeat
  2. temperatureto reflux under an inert atmosphere
  3. concentrationAfter 24 hours concentrate in vacuo
  4. additionConcentration of the product containing fractions

Sources & evidence

ORD record
ord-48efa1ddf4f64d71a05c40a4b2c33277
Source dataset
uspto-grants-1997_11
Patent number
US05684004

Reaction notes

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