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Dimethyl Sulfoxide → (R)-1-[3-(tertbutyldiphenyl-silyloxy)benzyl]-1-trimethylsilyoxy-2-cyclohexanone

HRID 379313
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 379313
C(Cl)(C(Cl)=O)=O.CS(C)=O.[C:11]([Si:15]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[O:16][C:17]1[CH:18]=[C:19]([CH:29]=[CH:30][CH:31]=1)[CH2:20][C@:21]1([OH:28])[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[OH:27])([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1>C(Cl)Cl.CN(C=O)C.C(N(CC)CC)C>[C:11]([Si:15]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[O:16][C:17]1[CH:18]=[C:19]([CH:29]=[CH:30][CH:31]=1)[CH2:20][C@:21]1([O:28][Si:15]([CH3:38])([CH3:32])[CH3:11])[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=[O:27])([CH3:14])([CH3:12])[CH3:13]
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Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 65578Oxalyl chlorideHCID 20691700(1R,2R)-1-[3-(tertbutyldiphenylsilyloxy)benzyl]-1,2-dihydroxycyclohexane

Produkt 1

HCID 86757468(R)-1-[3-(tertbutyldiphenyl-silyloxy)benzyl]-1-trimethylsilyoxy-2-cyclohexanoneAusbeute 16,6 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of (COCl)2 (3.4 ml) in CH2Cl2 (100 ml) was dropwise added DMSO (3.7 ml) at −78° C. After 10minutes, a solution of (1R,2R)-1-[3-(tertbutyldiphenylsilyloxy)benzyl]-1,2-dihydroxycyclohexane (12 g) in CH2Cl2(50 ml) was added to the above mixture at the same temperature. After 10 minutes, the mixture was added with triethylamine (15 ml) and allowed to stand at room temperature. After evaporating the solvent, the residue was partitioned between EtOAc and water. The organic layer was washed with water and brine. The organic solvent was evaporated in vacuo to give an oily compound. The oily compound was dissolved in DMF (50 ml) and then added with trimethylsilychloride (6.6 ml) and imidazole(7.0 g) at room temperature. After stirring for 5 hours, the mixture was partitioned between EtOAc and water. The organic solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give (R)-1-[3-(tertbutyldiphenylsilyloxy)benzyl]-1-trimethylsilyoxy-2-cyclohexanone (1.15 g).

Aufarbeitung

  1. customat −78° C
  2. waitAfter 10 minutes
  3. customto stand at room temperature
  4. customAfter evaporating the solvent
  5. customthe residue was partitioned between EtOAc and water
  6. washThe organic layer was washed with water and brine
  7. customThe organic solvent was evaporated in vacuo
  8. customto give an oily compound
  9. customthe mixture was partitioned between EtOAc and water
  10. customThe organic solvent was evaporated in vacuo
  11. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-91f65fd9404d4da1938e65b402e775b5
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06297267B1

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