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Hydrochloric Acid → 11-(5-Chloropentyl)-3,16-dihydroxy-estra-1,3,5(10)-trien-17-one

HRID 967724
Notes
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Reaction equation

HRID 967724 reaction equation
C([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH:18]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][Cl:28])([CH3:16])[C:14](=[O:29])[CH:13](Br)[CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=O)C.[OH2:31].[OH-].[Na+].Cl>N1C=CC=CC=1>[Cl:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH:18]1[CH2:17][C@@:15]2([CH3:16])[C@@H:11]([CH2:12][CH:13]([OH:31])[C:14]2=[O:29])[C@H:10]2[C@H:19]1[C:20]1[CH:21]=[CH:22][C:5]([OH:4])=[CH:6][C:7]=1[CH2:8][CH2:9]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69737675HCID 69737675, compound

Product 1

HCID 6973715111-(5-Chloropentyl)-3,16-dihydroxy-estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Procedure

A solution of 15.3 g of crude 3-acetoxy-16-bromo-11-(5-chloropentyl)-estra-1,3,5(10)-trien-17-one in 237 ml of pyridine is mixed with 79 ml of water and then with 50 ml of sodium hydroxide solution (1N) and stirred for 24 hours at room temperature. Then, 25 ml of hydrochloric acid (2N) is added, it is evaporated to the dry state in a vacuum, diluted with 11 of ethyl acetate, washed with hydrochloric acid (2N), washed neutral with water, washed with common salt solution, dried on sodium sulfate and evaporated to the dry state in a vacuum. 4.2 g of crude 11-(5-chloropentyl)-3,16-dihydroxy-estra-1,3,5(10)-trien-17-one is obtained, and after chromatography on silica gel with hexane/ethyl acetate, 2.5 g of pure 11-(5-chloropentyl)-3,16-dihydroxy-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. customit is evaporated to the dry state in a vacuum
  2. additiondiluted with 11 of ethyl acetate
  3. washwashed with hydrochloric acid (2N)
  4. washwashed neutral with water
  5. washwashed with common salt solution
  6. customdried on sodium sulfate
  7. customevaporated to the dry state in a vacuum

Sources & evidence

ORD record
ord-db30fde029854c1f929b1e175389b0e8
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06956031B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes