Acetic Acid → HCID 86739581, compound

HRID 358005Notes

Reaction equation

HRID 358005 reaction equation
[Cl:1][C@H:2]1[CH2:20][C@@:17]2([CH2:18][CH3:19])[C@@H:13]([CH:14]=[CH:15][C@:16]2([C:22]#[CH:23])[OH:21])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:24])[CH2:6][CH2:5]1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(O)(=O)C>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:25]([O:21][C@@:16]1([C:22]#[CH:23])[CH:15]=[CH:14][C@H:13]2[C@H:12]3[C@H:3]([C@@H:2]([Cl:1])[CH2:20][C@:17]12[CH2:18][CH3:19])[C@@H:4]1[C:9](=[CH:8][C:7](=[O:24])[CH2:6][CH2:5]1)[CH2:10][CH2:11]3)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 86739582HCID 86739582, compound

Product 1

HCID 86739581HCID 86739581, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

700 mg of 11β-chloro-17α-ethynyl-17β-hydroxy-18-methyl-4,15-estradien-3-one in 10 ml of pyridine is reacted at room temperature with the addition of 100 mg of 4-dimethylaminopyridine with 6 ml of acetic anhydride. The mixture is introduced, after 4 hours, into ice/water which contains acetic acid. The thus-precipitated product is vacuum-filtered, dissolved in ethyl acetate, and washed with water. The crude product is chromatographed on silica gel with hexane/acetone (0-10%), thus obtaining 510 mg of 17β-acetoxy-11β-chloro-17α-ethynyl-18-methyl-4,15-estradien-3-one as a foam.

Workup

  1. filtrationThe thus-precipitated product is vacuum-filtered
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water
  4. customThe crude product is chromatographed on silica gel with hexane/acetone (0-10%)

Sources & evidence

ORD record
ord-4337f38f7197450ea83a79ec034e3d88
Source dataset
uspto-grants-1984_08
Patent number
US04464365

Reaction notes

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