Sodium Hydroxide → Dihydrocholesterol

HRID 1721309

Reaktionsgleichung

Reaktionsgleichung von HRID 1721309
[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@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[OH-:28].[Na+]>C1COCC1.CO>[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@H:16]([CH2:17][C@@H:18]([OH:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 27238955-alpha-Cholestane

Produkt 1

HCID 6665DihydrocholesterolAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the fluorobenzoate (46, 27 mg, 0.051 mmol) in THF (2 mL) and MeOH (2 mL) was treated with 1M NaOH (0.2 mL, 0.2 mmol) and allowed to stand at ambient temperature for 7 h. After the solvent was evaporated, the residue was treated with CHCl3 (40 mL) and 10% Na2CO3 solution (30 mL); we then separated the layers, dried the organic layer over MgSO4, and filtered and evaporated it under reduced pressure. Purified on 2 g of Merck grade 60 flash silica gel using MeOH/CHCl3 (5:95) afforded 13 mg (60%) of 25-fluoro-3β-ol (47), mp 196°-198° C. EIMS (m/z): 428 (M+H), 413 (M-M3). 1H NMR: δ3.70 (m, 1H), 1.49 (s, 3H), 1.27 (s, 3H), 1.09 (s, 3H), 1.02 (d, 3H, J=6.4 Hz), 0.81 (s, 3H).

Aufarbeitung

  1. customAfter the solvent was evaporated
  2. additionthe residue was treated with CHCl3 (40 mL) and 10% Na2CO3 solution (30 mL)
  3. customwe then separated the layers
  4. dry with materialdried the organic layer over MgSO4
  5. filtrationfiltered
  6. customevaporated it under reduced pressure
  7. customPurified on 2 g of Merck grade 60 flash silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6c53ae5fd4df4e19b381e2fa4e2fc66b
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05510340

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