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Dimethyl Sulfoxide → (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde

HRID 1604831
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1604831
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([Si:15]([CH3:33])([CH3:32])[O:16][C@H:17]1[CH2:26][CH2:25][CH2:24][C@@:23]2([CH3:27])[C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:22]2[C@H:28]([CH3:31])[CH2:29][OH:30])([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC>C(Cl)Cl>[C:11]([Si:15]([CH3:33])([CH3:32])[O:16][C@H:17]1[CH2:26][CH2:25][CH2:24][C@@:23]2([CH3:27])[C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:22]2[C@H:28]([CH3:31])[CH:29]=[O:30])([CH3:13])([CH3:14])[CH3:12]
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Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21309368(S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol

Produkt 1

HCID 57255936(S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Swern reagent was prepared at -70° C. by adding slowly 1.70 ml of abs. DMSO to 0.947 ml of oxalylchloride, dissolved in 27 ml of CH2Cl2. 15 minutes later, 3.43 g of (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol (synthesis described in ref. Ex. 12), dissolved in 10 ml of CH2Cl2, were slowly added. After 0.25 h, 4.8 ml of NEt3 were added dropwise and the temperature allowed to reach -30° C. The reaction was quenched by pouring onto crushed ice/NH4Cl, extracted with ether, washed with water and brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=97/3) afforded (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde as colourless oil.

Aufarbeitung

  1. additionby adding slowly 1.70 ml of abs
  2. additionwere slowly added
  3. customto reach -30° C
  4. customThe reaction was quenched
  5. additionby pouring
  6. customonto crushed ice/NH4Cl
  7. extractionextracted with ether
  8. washwashed with water and brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-55f9ec093515472fabad034178d38f04
Quelldatensatz
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05994569

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