Hydrochloric Acid → HCID 57267156, compound

HRID 234729Notes

Reaction equation

HRID 234729 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 minutes. A solution of 7-oxo-3β-triisopropylsilyloxychol-5-en-24-oic acid (4) (5.38 g, 9.9 mmoles) in dry THF (16.5 ml) was added dropwise over 20 minutes 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 minutes and extracted with CH2Cl2 (three times). The combined s 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: δ0.70 (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 minutes
  5. extractionextracted with CH2Cl2 (three times)
  6. washwere washed with H2O and saturated brine
  7. dry with materialdried (MgSO4)
  8. customEvaporation in vacuo

Sources & evidence

ORD record
ord-f2b649c9d3604d5aa5d809ba09131a71
Source dataset
uspto-grants-1997_01
Patent number
US05595996

Reaction notes

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