Hydrochloric Acid → HCID 57267156, compound

HRID 1456008Notes

Reaction equation

HRID 1456008 reaction equation
N#N.[CH3:3][Mg]Cl.[O:6]=[C:7]1[CH:30]=[C:29]2[C@:24]([CH3:42])([CH2:25][CH2:26][C@H:27]([O:31][Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])[CH2:28]2)[C@@H:23]2[C@@H:8]1[C@H:9]1[C@:20]([CH3:43])([CH2:21][CH2:22]2)[C@@H:12]([C@H:13]([CH3:19])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1.[NH4+].[Cl-].Cl>C1COCC1>[CH3:3][C:7]1([OH:6])[CH:30]=[C:29]2[C@:24]([CH3:42])([CH2:25][CH2:26][C@H:27]([O:31][Si:32]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:34])[CH3:35])[CH:39]([CH3:41])[CH3:40])[CH2:28]2)[C@@H:23]2[C@@H:8]1[C@H:9]1[C@:20]([CH3:43])([CH2:21][CH2:22]2)[C@@H:12]([C@H:13]([CH3:19])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 54170027HCID 54170027, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 57267156HCID 57267156, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of anhydrous CeCl3 (1.21 g, 4.94 mmoles) was stirred at room temperature in a N2 atmosphere with dry THF (16.5 ml) for 2 hrs. MeMgCl (3N in THF, 16.5 ml) was added dropwise at room temperature, and the suspension was stirred from 30 min. A solution of 7-oxo-3b-triisopropylsilyloxychol-5-en-24-oic acid (4) (5.38 g, 9.9 mmoles) in dry THF (16.5 ml) was added dropwise over 20 min keeping the temperature of the reaction mixture below 20° with a cold H2O bath. After stirring at room temperature for 2 hrs, the reaction mixture was poured carefully with efficient stirring into a mixture of 90% saturated NH4Cl solution and 100 g of ice. The gummy suspension was acidified with 2N HCl, stirred well for 30 min and extracted with CH2Cl2 (three times). The combined extracts were washed with H2O and saturated brine and dried (MgSO4). Evaporation in vacuo gave 5.46 g of crude 5 as a tan foam. NMR(CDCl3) indicated a mixture of 7-isomers: δ 0.70 (two peaks, 18-Me); 5.14 & 5.20 (6-H) The mixture was used directly in the next reaction (Example 5).

Workup

  1. customthe temperature of the reaction mixture below 20°
  2. stirringAfter stirring at room temperature for 2 hrs
  3. additionthe reaction mixture was poured carefully
  4. stirringstirred well for 30 min
  5. extractionextracted with CH2Cl2 (three times)
  6. washThe combined extracts were washed with H2O and saturated brine
  7. dry with materialdried (MgSO4)
  8. customEvaporation in vacuo

Sources & evidence

ORD record
ord-2f935c5cdd324f388edea8ce92f14f5b
Source dataset
uspto-grants-1998_12
Patent number
US05843953

Reaction notes

Loading…