Sodium borohydride → Benzyl 9-hydroxynonanoate

HRID 1771050

Reaktionsgleichung

Reaktionsgleichung von HRID 1771050
[C:1]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](O)=[O:10].[BH4-].[Na+].[H][H].[B-](F)(F)(F)[O+](C)C>O1CCCC1.O>[OH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12]

Komponenten

7

Edukt 4

HCID 4311764Sodium borohydrideHCID 142502649-(Benzyloxy)-9-oxononanoic acidHCID 178418361HCID 178418361, VerbindungHCID 178494437HCID 178494437, Verbindung

Produkt 1

HCID 90034509Benzyl 9-hydroxynonanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The product from 11a (12.9 g; 46.3 mmol) was added in portions to a stirred mixture of sodium borohydride (1.70 g; 45.0 mmol) in dry tetrahydrofuran (25 mL). After the evolution of hydrogen subsided, a solution of boron trifluoride dimethyl etherate (4.6 mL; 5.7 g; 50 mmol) in dry tetrahydrofuran (15 mL) was added drop-wise. The exothermic reaction was moderated with a cold water bath. After stirring 4 h at ambient temperature, the reaction mixture was hydrolyzed with cold water (20 mL). The mixture was separated and the organic phase was evaporated; the residue was mixed with water (20 mL) and dichloromethane (70 mL) to give an emulsion that separated on standing overnight. The organic layer was washed with water (4×15 mL) until the washings were neutral to pH paper. Following drying (Na2SO4), filtration, and evaporation 11.95 g (98%) product was obtained (oil).

Aufarbeitung

  1. customThe exothermic reaction
  2. customwas moderated with a cold water bath
  3. customThe mixture was separated
  4. customthe organic phase was evaporated
  5. additionthe residue was mixed with water (20 mL) and dichloromethane (70 mL)
  6. customto give an emulsion that
  7. customseparated
  8. waiton standing overnight
  9. washThe organic layer was washed with water (4×15 mL) until the washings
  10. customFollowing drying
  11. filtration(Na2SO4), filtration
  12. customevaporation 11.95 g (98%) product
  13. customwas obtained (oil)

Quellen und Nachweise

ORD-Eintrag
ord-b66c3eb0870f4433b3c405259ff9572b
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249086B2

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