Water → 2-(2-{2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]ethoxy}-ethoxy)-tetrahydropyran

HRID 1159688Notes

Reaction equation

HRID 1159688 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:5]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[Na+].I[CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1.O>O1CCCC1>[Cl:1][CH2:2][CH2:3][C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:5]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5588852H-Pyran, tetrahydro-2-[2-(2-iodoethoxy)ethoxy]-HCID 539047244-[(1Z)-4-Chloro-1,2-diphenylbut-1-en-1-yl]phenol

Product 1

HCID 668526812-(2-{2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]ethoxy}-ethoxy)-tetrahydropyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Chloro-1,2-diphenyl-but-1-enyl)phenol (0.33 g, 0.001 mol) was dissolved in tetrahydrofuran (3 ml) under a nitrogen atmosphere. Sodium hydride (0.036 g, 0.0015 mol) was added to the solution and the mixture was stirred at room temperature for an hour. 2-[2-(2-iodo-ethoxy)-ethoxy)-tetrahydropyran (0.6 g, 0.002 mol) was added and the mixture was refluxed for 3 hours. After cooling and adding water the mixture was extracted three times with ethyl acetate. The organic phase was dried with sodium sulphate and evaporated to dryness. The residue was used in the next reaction step without further purification.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionwas extracted three times with ethyl acetate
  4. dry with materialThe organic phase was dried with sodium sulphate
  5. customevaporated to dryness
  6. customThe residue was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-5d9aeba4a9724e7d8918cf11f16ddd3b
Source dataset
uspto-grants-2010_10
Patent number
US07812197B2

Reaction notes

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