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Ozone → 3-(Tertbutyldiphenylsilyloxymethylene)-pentane-1,5-diol

HRID 741668
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 741668
O=[O+][O-].[Si:4]([O:21][CH:22]=[C:23]([CH2:27][CH2:28][OH:29])[CH2:24][CH2:25][OH:26])(C(C)(C)C)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[C:23]([C:22](=[C:23]([CH2:27][CH2:28][OH:29])[CH2:24][CH2:25][OH:26])[O:21][SiH:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:27])([CH3:24])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 187904493-(Tert-butyldiphenylsilyloxymethylene)-1,5-pentanediol

Produkt 1

HCID 1317195333-(Tertbutyldiphenylsilyloxymethylene)-pentane-1,5-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Ozone was bubbled through a -78° C. dry methanol (500 mL) solution of 3-(tert-butyldiphenylsilyloxymethylene)-1,5-pentanediol (17 g, 47 mmol) until a blue tint persisted (30 minutes). The reaction was purged with nitrogen (20 min.) and NaBH4 (17.6 g, 47 mmol) was added. The cold bath was removed and the reaction brought to room temperature. The reaction was concentrated in vacuo and the residue partitioned between ether and brine. The ether layer was concentrated and the residue eluted over a silica plug with 0-50% ethyl acetate/hexanes. The minor component was pooled and concentrated to yield the diol , 3-(tertbutyldiphenylsilyloxymethylene)-pentane-1,5-diol, 3.8 g (22%) of the desired diol as a colorless oil. Overall the yield for the three steps is 17%. MS.

Aufarbeitung

  1. custom(30 minutes)
  2. additionwas added
  3. customThe cold bath was removed
  4. custombrought to room temperature
  5. concentrationThe reaction was concentrated in vacuo
  6. customthe residue partitioned between ether and brine
  7. concentrationThe ether layer was concentrated
  8. washthe residue eluted over a silica plug with 0-50% ethyl acetate/hexanes
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bc3039f4aa6f45af8f7656f45664ab30
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05552396

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