Water → HCID 15871120, compound

HRID 1764973Notes

Reaction equation

HRID 1764973 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C@H:8]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@:10]([CH:35]=[O:36])([CH2:11][CH2:12][C:13]3[C@H:14]4[C@:26]([CH3:34])([CH2:27][CH2:28][C:29]=32)[C@@H:17]([C@H:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]4)[CH2:9]1.O.[OH-].[Na+]>O1CCCC1>[OH:36][CH2:35][C@:10]12[CH2:9][C@@H:8]([OH:7])[CH2:32][CH2:31][C@:30]1([CH3:33])[C:29]1[CH2:28][CH2:27][C@@:26]3([CH3:34])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@H:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:13]=1[CH2:12][CH2:11]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15871127HCID 15871127, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15871120HCID 15871120, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 56 mg lithiumaluminum hydride in 5 ml tetrahydrofuran is added to a solution of 200 mg 3β-hydroxy-5α-cholest-8-en-5-carbaldehyde in 20 ml tetrahydrofuran at room temperature. After being heated to 50° C. for two hours the reaction mixture is cooled to room temperature, 0.06 ml water, 0.06 ml of a sodium hydroxide solution (1 N) and 0.18 ml water are added subsequently. The resulting suspension is stirred for 15 minutes and filtered over anhydrous sodium sulphate. After evaporation of the solvent the residue is crystallized from ethylacetate to give 80 mg 5-(hydroxymethyl)-5α-cholest-8-en-3β-ol as a white solid.

Workup

  1. temperatureis cooled to room temperature
  2. filtrationfiltered over anhydrous sodium sulphate
  3. customAfter evaporation of the solvent the residue
  4. customis crystallized from ethylacetate

Sources & evidence

ORD record
ord-335d7f5640b547598464ed17596b6870
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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