Diethyl Ether → HCID 69046303, compound

HRID 1511533Notes

Reaction equation

HRID 1511533 reaction equation
[CH3:1][C:2](CC(CC(O)=O)=O)=[O:3].[CH3:11][C@@:12]12[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]1[C@@H:16]1[CH2:22][CH:23]=[C:24]3[CH2:29][C@@H:28]([OH:30])[CH2:27][CH2:26][C@:25]3([CH3:31])[C@H:15]1[CH2:14][CH2:13]2.CC[O:34]CC>N1C=CC=CC=1.C([O-])(=O)C.[Ag+]>[C:2]([C@H:29]1[C@@H:28]([OH:30])[CH2:27][CH2:26][C@@:25]2([CH3:31])[C:24]1=[CH:23][CH2:22][C@@H:16]1[C@@H:15]2[CH2:14][CH2:13][C@@:12]2([CH3:11])[C@H:17]1[CH2:18][C@@H:19]([OH:34])[C@@H:20]2[OH:21])(=[O:3])[CH3:1]

Participants

6

Reactant 3

HCID 3283Diethyl Ether2×HCID 5881DehydroepiandrosteroneHCID 54598443,5-Dioxohexanoic acid

Product 1

HCID 69046303HCID 69046303, compound

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 1049PyridineSolvent2×

Procedure

Compound 6 was dissolved in 30 mL of anhydrous ether and 10 mL of anhydrous pyridine. A solution of silver acetate (1.03 g, 1(914 mg, 2.98 mmol) in 5 mL of anhydrous pyridine was added. The reaction mixture was stirred under dark for 0.5 hr. A heavy greenish precipitate was deposited. Ether (50 mL) was added and precipitate was filtered off. The filtrate was under vacuum to dryness. The residue was purified by flash chromatograph on silica gel eluted with 50:50 ethyl acetate:hexanes to afford the title compound 7 (124 mg) as a white solid. Selected 1H NMR data: (CD3OD, 300 MHz): δ 5.78 (d, 1H, J=2.2 Hz), 5.34 (br, 1H), 4.02 (t, 1H, J=4.5 Hz), 3.52 (dt, 1H, J=7.7 Hz, 3.0 Hz), 3.37 (d, 1H, J=4.9 Hz), 2.03 (s, 3H), (1.12 (s, 3H), 0.75 (s, 3H). Melting Point: 152-153° C.

Workup

  1. filtrationprecipitate was filtered off
  2. customThe residue was purified by flash chromatograph on silica gel
  3. washeluted with 50:50 ethyl acetate

Sources & evidence

ORD record
ord-f4287d254620451e86a731041dc2014f
Source dataset
uspto-grants-2012_07
Patent number
US08217025B2

Reaction notes

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