Hydrochloric Acid → HCID 68143658, compound

HRID 1415055Notes

Reaction equation

HRID 1415055 reaction equation
C([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH:18]=[CH:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:21]C(=O)C)=[CH:16][C:15](=O)[CH2:14][CH2:13]4)C.C[Mg]Br.Cl>O1CCCC1>[CH2:6]([C@:5]12[CH2:14][CH2:13][C@@H:12]3[C@@H:17]4[C:16]([CH2:15][CH:8]([CH3:19])[C@H:9]3[C@@H:10]1[CH2:11][CH2:3][C@@H:4]2[OH:21])=[CH:5][C:4](=[O:21])[CH2:3][CH2:18]4)[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69868084HCID 69868084, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68143658HCID 68143658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add dl-13-ethyl-17β-acetoxygona-4,6-dien-3-one (2.0 g) in tetrahydrofuran (30 cc) to tetrahydrofuran (20 cc) containing 3 moles methyl magnesium bromide (16 cc) and cuprous chloride (299 mg) at 0°. Stir for 20 minutes and pour into ice-cold brine saturated with hydrogen chloride. Extract with ether and chromatograph on Grade 2.5 neutral alumina. To obtain the title compound, recrystallize from ethyl acetate-hexane (0.56 g), m.p. 152°-154°; λmax. KBr 2.98, 6.02 μ; λmax. EtOH 242 mμ (ε16,730).

Workup

  1. extractionExtract with ether and chromatograph on Grade 2.5 neutral alumina

Sources & evidence

ORD record
ord-4f375ee617164af88e786e35b7918c39
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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