Sodium Bicarbonate → HCID 86736879, compound

HRID 1701454Notes

Reaction equation

HRID 1701454 reaction equation
ClCC([O:5][C@@H:6]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:25]2[C@@H:24]([O:30][C:31](=[O:34])[CH2:32][Cl:33])[CH2:23][C@@:22]2([CH3:35])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:16]2([O:21][CH2:20][CH2:19][O:18]2)[CH3:17])[CH2:7]1)=O.C(=O)(O)[O-].[Na+]>CO>[Cl:33][CH2:32][C:31]([O:30][C@H:24]1[CH2:23][C@@:22]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C@@H:15]2[C:16]2([O:18][CH2:19][CH2:20][O:21]2)[CH3:17])[C@H:11]2[C@H:25]1[C@:26]1([CH3:29])[C@@H:8]([CH2:9][CH2:10]2)[CH2:7][C@H:6]([OH:5])[CH2:28][CH2:27]1)=[O:34]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86736880HCID 86736880, compound

Product 1

HCID 86736879HCID 86736879, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3α,11β-bischloroacetoxy-20,20-ethylenedioxy-5α-pregnane (1 g) in refluxing methanol was stirred whilst a saturated solution of sodium bicarbonate (2.5 ml) was added. The mixture was refluxed until reaction was judged complete (by t.l.c), most of the solvent was evaporated in vacuo and water was added. The crude product was collected by filtration and purified by preparative t.l.c. (ethyl acetate-petroleum ether 1:1) and crystallization from ethyl acetate-petroleum ether to give title compound m.p. 194°-202°, [α]D +44° (c 0.1).

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed until reaction
  3. custommost of the solvent was evaporated in vacuo and water
  4. additionwas added
  5. filtrationThe crude product was collected by filtration
  6. custompurified by preparative t.l.c
  7. custom(ethyl acetate-petroleum ether 1:1) and crystallization from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-49b163ec87a64d1abb65ba5da2f960c1
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

Loading…