Isopropanol-hcl-water → 17alpha-Allyl-17-hydroxy-13-propylgon-4-en-3-one

HRID 1077206Notes

Reaction equation

HRID 1077206 reaction equation
COC1CC2CC[C@H]3[C@H]4[C@@](CCC)(C(=O)CC4)CC[C@@H]3C=2CC=1.C([Mg]Br)C=C.[CH2:29]([C@@:32]1([OH:54])[C@:40]2([CH2:41][CH2:42][CH3:43])[C@H:35]([C@@H:36]3[CH2:51][CH2:50][C:49]4[CH2:48][C:47]([O:52]C)=[CH:46][CH2:45][C:44]=4[C@H:37]3[CH2:38][CH2:39]2)[CH2:34][CH2:33]1)[CH:30]=[CH2:31].Cl.C(O)(C)C.O>>[CH2:29]([C@@:32]1([OH:54])[C@:40]2([CH2:41][CH2:42][CH3:43])[C@H:35]([C@@H:36]3[CH2:51][CH2:50][C:49]4[C@H:44]([CH2:45][CH2:46][C:47](=[O:52])[CH:48]=4)[C@H:37]3[CH2:38][CH2:39]2)[CH2:34][CH2:33]1)[CH:30]=[CH2:31]

Participants

5

Reactant 4

HCID 21409480Isopropanol-hcl-waterHCID 541374823-Methoxy-13-propylgona-2,5(10)-dien-17-oneHCID 6814312217alpha-Allyl-3-methoxy-13-propylgona-2,5(10)-dien-17-olHCID 178455850HCID 178455850, compound

Product 1

HCID 6814481417alpha-Allyl-17-hydroxy-13-propylgon-4-en-3-one

Procedure

Treat dl-3-methoxy-13-propylgona-2,5(10)-dien-17-one (2.0 g) with allyl magnesium bromide to obtain a glass that is a mixture of dl-17α-allyl-3-methoxy-13-propylgona-2,5(10)-dien-17-ol (minor component) and the Δ5(10) -3-keto and Δ4 -3-keto compounds (major component). Hydrolyze the mixture (in two portions) with hydrochloric acid-isopropanol-water, then chromatograph and crystallize the resultant crude product to obtain the title compound (22% from the starting material), m.p. 135°-137°; ultraviolet absorption peak at 241.5 mμ (ε17,470), infrared maxima at 2.95 μ (OH), 6.03 μ, 6.18 μ (α,β-unsaturated carbonyl), 10.93 μ (R-CH=CH2).

Workup

  1. customto obtain a glass that
  2. customchromatograph and crystallize the resultant crude product

Sources & evidence

ORD record
ord-3ed19f88869e47deba939619f7ec5700
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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