Oxalic Acid → HCID 131724378, compound

HRID 49410Notes

Reaction equation

HRID 49410 reaction equation
CO[C:3]1[CH2:4][C:5]2[CH2:6][C@@H:7]([CH3:24])[C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@:9]23[CH2:23][C@@H:10]2[CH2:11][C@H:12]1[CH2:21]O.C(O)(=O)[C:26](O)=[O:27].C(=O)([O-])[OH:32].[Na+]>CO.O1CCCC1.O>[OH:27][CH2:26][CH2:21][C@@H:12]1[CH2:11][C@H:10]2[CH2:23][C@@:9]32[C@H:8]2[C@H:17]([CH2:16][CH2:15][C@:13]13[CH3:14])[C:18]1[CH2:19][CH2:20][C:3](=[O:32])[CH2:4][C:5]=1[CH2:6][C@H:7]2[CH3:24]

Participants

7

Reactant 3

HCID 971Oxalic AcidHCID 516892Sodium BicarbonateHCID 69625019(7alpha,14beta,15beta,17alpha)-3-Methoxy-7-methyl-14,15-methyleneestra-2,5(10)-diene-17-methanol

Product 1

HCID 131724378HCID 131724378, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (7α,14β,15β,17α)-3-methoxy-7-methyl-14,15-methyleneestra-2,5(10)-diene-17-methanol (Example 1, step vi; 7.38 g) in a mixture of methanol (68 ml) and tetrahydrofuran (48 ml) was treated with a solution of oxalic acid (2.38 g) in water (40 ml). After 1 h stirring at room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (7α,14β,15β,17α)-17-(hydroxyethyl)-7-methyl-14,15-methyleneestr-5(10)-en-3-one (4.27 g). 1H NMR (CDCl3) δ3.69 (m, 1H), 3.51 (t, 1H, J=9.0 Hz), 2.72 (bs, 2H), 2.46 (bs, 2H), 1.04 (s, 3H), 0.69 (d, 3H, J=7.1 Hz), 0.48(dd, 1H, J=8.3 and 5.1 Hz), 0.27 (dd, 1H, J=5.1 and 3.1 Hz).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3ce938e8ba948cdb819560530d83ab7
Source dataset
uspto-grants-2004_03
Patent number
US06706700B2

Reaction notes

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