Citric Acid → HCID 67680488, compound

HRID 865636Notes

Reaction equation

HRID 865636 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3([OH:25])[CH:12]=[CH:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2].Cl[CH2:27][O:28][CH2:29][CH3:30].C(N(C(C)C)CC)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3([O:25][CH2:27][O:28][CH2:29][CH3:30])[CH:12]=[CH:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 11163795HCID 11163795, compound

Product 1

HCID 67680488HCID 67680488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9.20 g of 3β-acetoxy-14β-hydroxy-5β-androst-15-en-17-one (G. Groszek et al., Bull. Pol. Acad. Sci., Chem., 34, 1986, 313), 11 ml of ethyl chloromethyl ether, 54 ml of diisopropylethylamine in 750 ml of dichloromethane was heated at reflux for 24 hrs. The solution was then cooled and poured into 500 ml of aq. 8% citric acid solution. The lower layer was separated, washed with water, dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by chromatography using cyclohexane/chloroform/acetone 80/10/10 as eluant to give 6.10 g of 3β-acetoxy-14β-ethoxymethoxy-5β-androst-15-en-17-one, as a white solid.

Workup

  1. temperatureat reflux for 24 hrs
  2. temperatureThe solution was then cooled
  3. customThe lower layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-849d7c13995841419ab33ca5ab5db972
Source dataset
uspto-grants-1996_10
Patent number
US05567694

Reaction notes

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