Sodium borohydride → 3-(2-{[Tert-butyl(diphenyl)silyl]oxy}ethyl)cyclobutanol

HRID 1183962

Reaktionsgleichung

Reaktionsgleichung von HRID 1183962
[Si:1]([O:18][CH2:19][CH2:20][CH:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1>[Si:1]([O:18][CH2:19][CH2:20][CH:21]1[CH2:24][CH:23]([OH:25])[CH2:22]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 575657723-(2-{[Tert-butyl(diphenyl)silyl]oxy}ethyl)cyclobutanone

Produkt 1

HCID 575657453-(2-{[Tert-butyl(diphenyl)silyl]oxy}ethyl)cyclobutanolAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(2-{[Tert-butyl(diphenyl)silyl]oxy}ethyl)cyclobutanone (5.11 g, 14.5 mmol) (WO 2006063281) was dissolved in tetrahydrofuran (120 mL). Sodium borohydride (548 mg, 14.5 mmol) was added and the reaction was stirred overnight at room temperature. The reaction was quenched with water and saturated aqueous sodium bicarbonate and stirred for 20 min until the bubbling ceased. The reaction mixture was diluted with ether and the aqueous layer was extracted with ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo to give 3-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)cyclobutanol (3.58 g, 69.6%) as a clear oil. Partial 1H NMR indicated a ˜3.5:1 mix of cis-trans isomers. (CDCl3, δ ppm, key peaks are 4.08 (quintet, J=7.42, 0.78H) and 4.34 (quintet, J=6.83, 0.22H).

Aufarbeitung

  1. customThe reaction was quenched with water and saturated aqueous sodium bicarbonate
  2. stirringstirred for 20 min until the bubbling
  3. additionThe reaction mixture was diluted with ether
  4. extractionthe aqueous layer was extracted with ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d182d90039e64e1aa36935a568663b28
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664401B2

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