Hydrochloric Acid → HCID 68145829, compound

HRID 1077188Notes

Reaction equation

HRID 1077188 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20]C)[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:22][CH3:23])[CH3:2].CO.Cl>O1CCCC1.O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:22][CH3:23])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 54300386HCID 54300386, compound

Product 1

HCID 68145829HCID 68145829, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Add 13β-ethyl-3, 17β-dimethoxy-gona-2,5(10)-diene (0.8 g.) in tetrahydrofuran (5 cc.) to methanol (72 cc.) in an atmosphere of nitrogen and add a mixture of hydrochloric acid (4.8 cc.) and water (3.2 cc.). Add a further 10 cc. of tetrahydrofuran and after 1 hour dilute the solution with water and extract with ether. Wash, dry and evaporate the ethereal extracts and chromatograph the residue on neutral alumina. Remove impurities by elution with benzene. Wash the column with ether, evaporate the eluate and recrystallize the residue from hexane to obtain the title compound (0.2 g.), m.p. 117°-119°; ultraviolet absorption ξ max. 240 mμ (ε15,800); infrared spectrum (KBr disc) 6.0, 6.2, 8.8, 9.05 μ.

Workup

  1. additionadd
  2. additionAdd a further 10 cc
  3. extractionextract with ether
  4. washWash
  5. customdry
  6. customevaporate the ethereal extracts and chromatograph the residue on neutral alumina
  7. washRemove impurities by elution with benzene
  8. washWash the column with ether
  9. customevaporate the eluate and
  10. customrecrystallize the residue from hexane

Sources & evidence

ORD record
ord-7c2191183fa340e0ba8fa515de32f997
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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