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Water → (4R,6S) 6-[2-(2,4-dichlorophenyl)ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-on

HRID 1719629
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1719629
C1(S([CH:10]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[CH2:11][C@H:12]2[O:17][C@@H:16]([O:18]C)[CH2:15][C@H:14]([O:20]CC3C=CC=CC=3)[CH2:13]2)(=O)=O)C=CC=CC=1.P(O)([O-])([O-])=O.[Na+].[Na+].O>CO.[Na].[Hg]>[Cl:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[CH2:10][CH2:11][C@@H:12]1[O:17][C:16](=[O:18])[CH2:15][C@H:14]([OH:20])[CH2:13]1
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Komponenten

6

Edukt 3

HCID 962WaterHCID 24203Sodium Phosphate, DibasicHCID 228261981-(2,4-dichlorophenyl)-2-(4(R)-benzyloxy-2(R)-methoxy-3,4,5,6-tetrahydro-2H-pyran-6(S)-yl)ethyl phenyl sulfone

Produkt 1

HCID 13186032(4R,6S) 6-[2-(2,4-dichlorophenyl)ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-onAusbeute 125,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9837419
Sodium amalgam
Katalysator
2×
HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 1-(2,4-dichlorophenyl)-2-(4(R)-benzyloxy-2(R)-methoxy-3,4,5,6-tetrahydro-2H-pyran-6(S)-yl)ethyl phenyl sulfone (0.06 g, 0.11 mmole) and anhydrous disodium phosphate (0.065 g, 0.45 mmoles) in dry methanol (5 ml) was added pulverized 5% sodium amalgam (0.2 g). The mixture was stirred at room temperature for twenty hours, during which time an additional 0.4 g of 5% sodium amalgam was added in three portions. The reaction mixture was poured into water and extracted with ether. The ether solution was dried (MgSO4), filtered, and the solvent evaporated in vacuo to give the title compound as a colorless viscous oil (0.04 g); 'H NMR (CDCl3) δ 1.53 (1H, ddd), 1.58-1.88 (4H, m), 2.06 (1H, m), 2.70 (1H, ddd), 2.95 (1H, ddd), 3.42 (3H, s), 3.76 (1H, p), 4.16 (1H, d), 4.52 (1H, d), 4.65 (1H, d), 4.78 (1H, dd), 7.13-7.40 (8H, m).

Aufarbeitung

  1. additionwas added
  2. additionwas added in three portions
  3. extractionextracted with ether
  4. dry with materialThe ether solution was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-993701b409a842018010fc2d9c36be7f
Quelldatensatz
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04540796

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