Hydrochloric Acid → HCID 70020134, compound

HRID 651503Notes

Reaction equation

HRID 651503 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][Si](C)(C)C(C)(C)C.O1[C:37]2=[C:38]3[C@H:29]([C@H:30]4[C@@:34]([CH2:36]2)([CH3:35])[C:33](=[O:39])[CH2:32][CH2:31]4)CCC2[C@@]13CCCC2.Cl.[C:41](=[O:44])(O)[O-].[Na+]>O1CCCC1.[Cu](Cl)Cl>[OH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C@H:37]1[CH2:36][C@@:34]2([CH3:35])[C@@H:30]([CH2:31][CH2:32][C:33]2=[O:39])[C@H:29]2[C:38]1=[C:29]1[C:30]([CH2:31][CH2:32]2)=[CH:34][C:41](=[O:44])[CH2:37][CH2:38]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5462224MagnesiumHCID 11045996Silane, [(9-bromononyl)oxy](1,1-dimethylethyl)dimethyl-HCID 69989111HCID 69989111, compound

Product 1

HCID 70020134HCID 70020134, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

5.2 cm3 of a solution of magnesium compound (0.42 M/l) prepared from the product obtained in Stage A and 2.3 cm3 of tetrahydrofuran is cooled down to 0°/+2° C. 30 mg of copper chloride is added, agitation is carried out for 30 minutes, followed by cooling down to −30° C. and 330 mg of 3-ethylenedioxy 5 (10-epoxy estr-9(11)-ene-17-one dissolved in 2 cm3 of tetrahydrofuran is added and agitation is carried out for 45 minutes. 6 cm3 of 2M hydrochloric acid is added and agitation is carried out for 2 hours at ambient temperature. The reaction medium is poured into a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate, washing with salt water, drying and evaporating the solvent. After chromatographing the residue on silica (eluant: ethyl acetate-cyclohexane 6-4), 192 mg of expected product is obtained.

Workup

  1. temperatureis cooled down to 0°/+2° C
  2. additionis added
  3. waitagitation is carried out for 45 minutes
  4. waitagitation is carried out for 2 hours at ambient temperature
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with salt water
  7. customdrying
  8. customevaporating the solvent

Sources & evidence

ORD record
ord-0271b8ed75bd4fed965fc92500715696
Source dataset
uspto-grants-2001_08
Patent number
US06281204B1

Reaction notes

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