Cholesterol → HCID 11453592, compound

HRID 1447971Notes

Reaction equation

HRID 1447971 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[CH2:29]([O:31][CH2:32]OCC)[CH3:30].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH2:29]([O:31][CH2:32][O:19][C@H:18]1[CH2:20][CH2:21][C@@:22]2([CH3:23])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:17]1)[CH3:30]

Participants

4

Reactant 3

HCID 5997CholesterolHCID 10024DiethoxymethaneHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 11453592HCID 11453592, compound

Procedure

20 g. of cholesterol is dissolved in 300 ml. of formaldehyde diethylacetal, combined under agitation at room temperature with 30 g. of kieselguhr and in incremental portions with 15 g. of phosphorus pentoxide, and agitated for 4 hours at room temperature. The product is filtered off from the insoluble matter, washed with formaldehyde diethylacetal, and the solvent is distilled off under vacuum. The residue is crystallized at 0° C. After adding sodium bicarbonate solution, the crude product is vacuum-filtered, washed with water, and, after drying, 22.5 g. of 3β-ethoxymethoxy-5-cholestene is obtained. The compound, recrystallized from ethyl acetate, melts at 64°-66° C.

Workup

  1. customcombined under agitation at room temperature with 30 g
  2. filtrationThe product is filtered off from the insoluble matter
  3. washwashed with formaldehyde diethylacetal
  4. distillationthe solvent is distilled off under vacuum
  5. customThe residue is crystallized at 0° C
  6. additionAfter adding sodium bicarbonate solution
  7. filtrationthe crude product is vacuum-filtered
  8. washwashed with water
  9. customafter drying

Sources & evidence

ORD record
ord-98388c43e5674145ad6d124803c5b9bc
Source dataset
uspto-grants-1979_12
Patent number
US04179336

Reaction notes

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