Dimethylformamide → HCID 70467257, compound

HRID 64729Notes

Reaction equation

HRID 64729 reaction equation
[CH:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH2:12]([C@H:14]1[CH2:19][C@H:18]2[C@H:20]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C@H:15]1[O:33][C:34](=[O:37])[CH2:35]Br)[C@@H:28]1[C:23](=[CH:24][C:25](=[O:32])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)[CH3:13].CN(C=O)C>CC(C)=O>[CH2:12]([C@H:14]1[CH2:19][C@H:18]2[C@H:20]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C@H:15]1[O:33][C:34](=[O:37])[CH2:35][O:8][C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:9])[C@@H:28]1[C:23](=[CH:24][C:25](=[O:32])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7413Cyclohexanecarboxylic acidHCID 14798Sodium HydroxideHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 70467257HCID 70467257, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 20 ml of acetone is dissolved 0.64 g of cyclohexanecarboxylic acid, and 2.5 ml of 2N-NaOH and then 1.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 20 ml of DMF are serially added to the above solution. The mixture is refluxed for 5 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is then chromatographed on a silica gel column. Following passage of 200 ml of n-hexane-diisopropyl ether (6:4), elution is carried out with 600 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.98 g of the above-identified compound as a light-yellow viscous oil.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. additiontreated in the same manner as Example 26
  3. customThe reaction mixture is then chromatographed on a silica gel column
  4. washpassage of 200 ml of n-hexane-diisopropyl ether (6:4), elution
  5. additionis carried out with 600 ml of a 1:1 mixture of the same solvents
  6. customThe eluate is evaporated under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-82d35332a58445748650ceff7a8713cd
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

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