Water → HCID 67536381, compound

HRID 42085Notes

Reaction equation

HRID 42085 reaction equation
C1CO[C:8]23OCCO[C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([CH2:16][C:17](=[CH2:28])[CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.[OH2:40].C([O-])(O)=O.[Na+]>CC(C)=O>[CH2:28]=[C:17]1[CH:18]2[C@:23]([CH3:24])([CH2:22][CH2:21][C:20](=[O:40])[CH2:19]2)[C@@H:25]2[C@H:15]([C@H:6]3[C@@:4]([CH2:27][CH2:26]2)([CH3:5])[C:3](=[O:2])[CH2:8][CH2:7]3)[CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 6753593917,17-Bis(ethylendioxy)-6-methyleneandrostane

Product 1

HCID 67536381HCID 67536381, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 3,3:17,17-bis(ethylendioxy)-6-methyleneandrostane (1.05 g) and pTSA.H2O (2.46 g) in acetone (105 mL) was stirred at room temperature for 3 h. The solution was neutralized by addition of 5% aqueous NaHCO3 and acetone was evaporated. The aqueous suspension was extracted with CH2Cl2 (3×). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness to give the title compound II-ac in 87% yield. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.85 (1H, m), 4.50 (1H, m), 2.63-1.02 (20H, m), 0.92 (3H, s), 0.86 (3H, s).

Workup

  1. customwas evaporated
  2. extractionThe aqueous suspension was extracted with CH2Cl2 (3×)
  3. washThe combined organic extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5b12658c6c454522b0b3d55dc323d513
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

Loading…