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Raloxifene → 6-Acetoxy-2-(4-acetoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene

HRID 1649613
Notes
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Reaction equation

HRID 1649613 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10](=[O:26])[C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)=[C:8]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[S:7][C:6]=2[CH:34]=1.[O:35]1[CH2:39][CH2:38]CC1.C(=O)([O-])[O-].[K+].[K+].[C:46](OC(=O)C)(=[O:48])[CH3:47]>C(Cl)(Cl)Cl>[C:46]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10](=[O:26])[C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]4)=[CH:15][CH:16]=3)=[C:8]([C:27]3[CH:28]=[CH:29][C:30]([O:33][C:39](=[O:35])[CH3:38])=[CH:31][CH:32]=3)[S:7][C:6]=2[CH:34]=1)(=[O:48])[CH3:47]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5035RaloxifeneHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 11430Potassium Carbonate

Product 1

HCID 109952786-Acetoxy-2-(4-acetoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Procedure

Two g. of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene was dissolved in 30 ml. of tetrahydrofuran, and 3.5 g. of potassium carbonate was added. The vessel was blanketed with nitrogen and 0.9 g. of acetic anhydride was added. The mixture was stirred at ambient temperature for 2 hours, and then under reflux for 2 hours more. The mixture was then cooled, and to it was added 200 ml. of chloroform. The mixture was washed with 100 ml. of aqueous sodium chloride solution, and the organic layer was dried over magnesium sulfate, filtered and evaporated to dryness under vacuum at 40° C. A white foam was obtained, which was determined to be the desired product.

Workup

  1. temperatureunder reflux for 2 hours more
  2. temperatureThe mixture was then cooled
  3. additionto it was added 200 ml
  4. washThe mixture was washed with 100 ml
  5. dry with materialof aqueous sodium chloride solution, and the organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness under vacuum at 40° C
  8. customA white foam was obtained

Sources & evidence

ORD record
ord-fe882985eef640c38a91539ddaec3a9f
Source dataset
uspto-grants-1983_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04418068

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes