Sodium Chloride → HCID 70582518, compound

HRID 1395235Notes

Reaction equation

HRID 1395235 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:6]([CH2:7][CH:8]=[C:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@@:10]3([CH2:32][CH3:33])[C:11](=[O:31])[CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5]1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[Na+].[Cl-].C(O[C@H]1CC[C@@]2(C)[C@@H](CC=C3[C@@H]2CC[C@@]2(C)[C@@]3(CC)[C@@H](O)C[C@@H]2[C@H](C)CCCC(C)C)C1)C>CCOCC>[CH2:1]([O:3][C@H:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:6]([CH2:7][CH:8]=[C:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@@:10]3([CH2:32][CH3:33])[C@H:11]([OH:31])[CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:19])[CH3:20])[CH2:5]1)[CH3:2]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 70581465HCID 70581465, compoundHCID 70581570HCID 70581570, compound

Product 1

HCID 70582518HCID 70582518, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 3β-ethoxy-14α-ethyl-5α-cholest-7-en-15-one (1.0 g; 2.19 mmol) in ether (100 ml) was added lithium aluminum hydride (2.0 g; 52.7 mmol). After stirring for 2 hours at room temperature, the reaction mixture was cooled to 0° C. and ice was cautiously added to decompose the unreacted hydride. The resulting mixture was poured into a 0.35 M NaCl solution and extracted thoroughly with ether containing methylene chloride (5%). The combined extracts were dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The resulting residue (0.97 g) was crystallized from acetone-water to give a mixture (0.94 g; 94% yield) of 3β-ethoxy-14α-ethyl-5α-cholest-7-en-15β-ol and 3β-ethoxy-14α-ethyl-5α-cholest-7-en-15α-ol. The following structures for the compounds were shown by i.r., n.m.r., and m.s. analyses: ##STR38##

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. additionice was cautiously added
  3. extractionextracted thoroughly with ether
  4. additioncontaining methylene chloride (5%)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe resulting residue (0.97 g) was crystallized from acetone-water

Sources & evidence

ORD record
ord-ec42f3663de943cd8e0f83517b2165d6
Source dataset
uspto-grants-1980_05
Patent number
US04202891

Reaction notes

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