Sodium periodate → 3-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

HRID 1506373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506373
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]([OH:32])CO)=[CH:23][CH:22]=5)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]=[O:32])=[CH:23][CH:22]=5)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 23667635Sodium periodateHCID 671718521-(3-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol

Produkt 1

HCID 866698873-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol (Preparation 26B, 0.097 g, 0.223 mmol) in methanol (2 mL) at 0° C. was added a solution of sodium periodate (0.057 g, 0.268 mmol) in water (2 mL) dropwise. The white heterogeneous reaction mixture was stirred for 40 mins. at 0° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried over sodium sulfate, concentrated, dried in vacuo to yield 3-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde. LC/MS M+1=402.23.

Aufarbeitung

  1. customThe white heterogeneous reaction mixture
  2. customat 0° C. and partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1a5129683bbe485fafc31387cfad825d
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216972B2

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