Hydrochloric Acid → HCID 68145884, compound

HRID 1415005Notes

Reaction equation

HRID 1415005 reaction equation
[CH2:1]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH2:15][CH:16]=[C:17]([O:22]C)[CH2:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])[CH2:2][CH2:3][CH3:4].Cl>O.CO>[CH2:1]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C@@H:14]4[C:19]([CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])=[CH:18][C:17](=[O:22])[CH2:16][CH2:15]4)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53821585HCID 53821585, compound

Product 1

HCID 68145884HCID 68145884, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Shake 13β-n-butyl-3-methoxy-gona-2,5(10)-dien-17β-ol (0.49 g.) with concentrated hydrochloric acid (1.2 cc.) in water (0.8 cc.) and methanol (18 cc.) until solution is complete. Allow to stand 2 hours at room temperature, pour the mixture into water and extract the product with ether. Evaporate the washed and dried ether extracts and recrystallize the solid from a mixture of ethyl acetate and ether to obtain the title compound (0.32 g.), m.p. 169°-70°; ultraviolet absorption peak at 240 mμ (ε17,000); infrared absorption peaks at 2.92, 6.01 μ.

Workup

  1. extractionextract the product with ether
  2. customEvaporate the
  3. washwashed
  4. customdried ether extracts and recrystallize the solid
  5. additionfrom a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-d7592992bfe44aabb89511755d9e74b1
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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