Sodium borohydride → HCID 71089357, Verbindung

HRID 2273375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2273375
[CH2:1]([C:7]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:19]2[CH:18]=[C:17]3[C:20](=[O:24])[CH:21]([CH3:23])[CH2:22][C:16]3=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[BH4-].[Na+]>C1COCC1.C(O)C>[CH2:25]([C:7]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:19]2[CH:18]=[C:17]3[CH:20]([OH:24])[CH:21]([CH3:23])[CH2:22][C:16]3=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 71089296HCID 71089296, Verbindung

Produkt 1

HCID 71089357HCID 71089357, VerbindungAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 1000 mL round flask, 9,9-dihexyl-2-methyl-2,3-dihydrocyclopenta[b]fluoren-1(9H)-one (85 g, 211.1 mmol) was dissolved in THF 400 mL and ethanol 400 mL, and then stirred. Sodium borohydride (NaBH4) (10 g, 265.0 mmol) was added to the reaction product in five lots, and then stirred for 12 hours. The resultant mixture, after removal of solvent, was dissolved in ethylacetate, and then washed with water three times. The organic layer was dried over magnesium sulfate, followed by removal of volatile materials and drying, to thereby obtain 82.0 g of 9,9-dihexyl-2-methyl-1,2,3,9-tetrahydrocyclopenta[b]fluoren-1-ol (yield: 96.0%) (two isomers), as highly viscous oil.

Aufarbeitung

  1. customThe resultant mixture, after removal of solvent
  2. dissolutionwas dissolved in ethylacetate
  3. washwashed with water three times
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customfollowed by removal of volatile materials
  6. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-7b4a6be3fd84430c8523ec0cb7f14e62
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120884B2

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