Hydrochloric Acid → HCID 13061708, compound

HRID 2199016Notes

Reaction equation

HRID 2199016 reaction equation
[CH3:1]/[CH:2]=[C:3]1/[CH2:4][CH2:5][C@@H:6]2[C@:20]/1([CH3:21])[CH2:19][CH2:18][C@H:17]1[C@H:7]2[C@H:8]([OH:23])[CH2:9][C@H:10]2[C@:15]1([CH3:16])[CH2:14][CH2:13][C@@H:12]([OH:22])[CH2:11]2.N1[CH:29]=[CH:28]C=CC=1.[C:30](OC(=O)C)(=[O:32])[CH3:31].Cl.[OH2:38]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:30]([O:22][C@@H:12]1[CH2:13][CH2:14][C@@:15]2([CH3:16])[C@H:10]([CH2:9][C@@H:8]([O:23][C:28](=[O:38])[CH3:29])[C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:6]3[CH2:5][CH2:4]/[C:3]/2=[CH:2]/[CH3:1])[CH2:11]1)(=[O:32])[CH3:31]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13061706HCID 13061706, compound

Product 1

HCID 13061708HCID 13061708, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 0.60 g (0.00188 mol) of (Z)-3α,5β,7α-pregn-17(20)-ene-3,7-diol and 30 ml of dry toluene was added 1.8 ml (ca. 1.84 g=0.023 mol) of dry pyridine, 1.8 ml (ca. 1.66 g=0.016 mol) of acetic anhydride and 0.016 g (0.00013 mol) of 4-dimethylaminopyridine. The mixture was stirred under argon atmosphere for 18 hr. and then poured into 100 ml of water, acidified with 1 N HCl and extracted with 3×50 ml of ethyl acetate. The combined organic phases were washed with water until neutral and then dried over anhydrous sodium sulfate. Filtration and evaporation of the solvent in vacuo gave 0.789 g of crude product. TLC revealed an incomplete reaction so the above procedure was repeated. The product was recrystallized from methanol to afford 0.566 g (75%) of (Z)-3α,5β,7α-pregn-17(20)-ene-3,7-diol diacetate. The analytical sample, recrystallized twice from methanol, had mp 92°-93° C.

Workup

  1. extractionextracted with 3×50 ml of ethyl acetate
  2. washThe combined organic phases were washed with water until neutral and
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. filtrationFiltration and evaporation of the solvent in vacuo
  5. customgave 0.789 g of crude product
  6. customan incomplete reaction so the above procedure
  7. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-e9cab88296d741a39c581a3d80d3aeb5
Source dataset
uspto-grants-1982_11
Patent number
US04360470

Reaction notes

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