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Methanol → 12-(Cholest-5-en-3beta-oxy)dodecan-1,3-diol

HRID 1471361
Notes
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Reaction equation

HRID 1471361 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]([OH:42])[CH2:39][CH:40]=[O:41])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].CO.[BH4-].[Na+]>O1CCOCC1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]([OH:42])[CH2:39][CH2:40][OH:41])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 8666535212-(Cholest-5-en-3beta-oxy)-3-hydroxydodecanal

Product 1

HCID 8666535312-(Cholest-5-en-3beta-oxy)dodecan-1,3-diolYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 100 mL round-bottomed flask was 12-(Cholest-5-en-3β-oxy)-3-hydroxydodecanal (1.90 g, 3.25 mmol) dissolved in 1,4-Dioxane (10 ml) to give a colorless solution. MeOH (5 ml) was added slowly and only enough was added to keep the aldehyde in solution. SODIUM BOROHYDRIDE (0.184 g, 4.87 mmol) was added to the stirring solution which was then allowed to stir for 2 hours at room temperature. The reaction mixture was quenched by addition of 1N HCl (2 mL). The mixture was diluted to 100 mL with water and extracted with ethyl acetate (3×50 mL). The organic phase was combined, washed with brine (1×50 mL), dried over Na2SO4, filtered and concentrated to give 12-(Cholest-5-en-3β-oxy)dodecan-1,3-diol (1.85 g, 3.15 mmol, 97% yield) as a colorless wax. 1H NMR (300 MHz, CDCl3) δ0.69 (3H, s); 0.83-2.07 (58H, m); 2.13-2.28 (1H, m); 2.32-2.43 (1H, m); 3.14 (1H, tt, J=11.2, 4.4 Hz); 3.46 (2H, t, J=6.8 Hz); 3.60-4.19 (3H, m); 5.36 (1H, d, J=5.2 Hz).

Workup

  1. customIn a 100 mL round-bottomed flask was
  2. customto give a colorless solution
  3. additiononly enough was added
  4. customThe reaction mixture was quenched by addition of 1N HCl (2 mL)
  5. additionThe mixture was diluted to 100 mL with water
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. washwashed with brine (1×50 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6585fa2c5768442e96a73ca5345c2394
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012225B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes