Sodium borohydride → HCID 10902156, Verbindung

HRID 582902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582902
[O:1]1[C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:2]1[C:3](OC)=[O:4].[BH4-].[Na+]>O1CCCC1>[O:1]1[C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:2]1[CH2:3][OH:4]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 56999066HCID 56999066, Verbindung

Produkt 1

HCID 10902156HCID 10902156, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In 500 ml of tetrahydrofuran were suspended 62.4 g (0.2 mol) of the methyl (2S,3R)-2,3-epoxyoctadecanoate (V-1) prepared in Example 3-(3) and 7.4 g (0.2 mol) of NaBH4, followed by heat refluxing for 3 hours. After confirming disappearance of the compound (V-1) by TLC, tetrahydrofuran was evaporated. To the residue were added 20 ml of water and then 500 ml of a saturated ammonium chloride aqueous solution to adjust to pH 5 to 6, and the mixture was extracted with 500 ml of ethyl acetate. After drying, ethyl acetate was removed by evaporation, and the resulting crude crystals were recrystallized from heptane to obtain 42.6 g (0.15 mol; yield: 75%) of (2R,3R)-2,3-epoxyoctadecanol (melting point: 77 to 78° C.). Optical rotation [α]D25 =+24.5° (c=0.285, CHCl3)

Aufarbeitung

  1. temperatureby heat
  2. temperaturerefluxing for 3 hours
  3. customwas evaporated
  4. additionTo the residue were added 20 ml of water
  5. extractionthe mixture was extracted with 500 ml of ethyl acetate
  6. customAfter drying
  7. customethyl acetate was removed by evaporation
  8. customthe resulting crude crystals were recrystallized from heptane

Quellen und Nachweise

ORD-Eintrag
ord-0b1b40ca4bb641a3a0d2421a717da038
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925792

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