Triphenylphosphine → methyl 3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoate

HRID 20589

Reaktionsgleichung

Reaktionsgleichung von HRID 20589
[CH:1]([Si:4]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[O:5][CH2:6][C@H:7]([OH:9])[CH3:8])([CH3:3])[CH3:2].O[C:17]1[CH:18]=[C:19]([CH:24]=[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=1)[C:20]([O:22][CH3:23])=[O:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:28]([O:27][C:25]1[CH:24]=[C:19]([CH:18]=[C:17]([O:9][C@@H:7]([CH3:8])[CH2:6][O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:10]([CH3:12])[CH3:11])[CH:13]([CH3:15])[CH3:14])[CH:26]=1)[C:20]([O:22][CH3:23])=[O:21])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoateHCID 57504697(2R)-1-{[Tri(propan-2-yl)silyl]oxy}propan-2-ol

Produkt 1

HCID 53629622methyl 3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoateAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(2R)-1-[(Triisopropylsilyl)oxy]propan-2-ol (56.1 g, 242 mmol) was added to a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (50 g, 194 mmol) and triphenylphosphine (63.5 g, 242 mmol) in dry THF (500 mL), at to 0° C., followed by addition of DIAD (47.6 mL, 242 mmol) over 45 minutes under an argon atmosphere. The reaction was stirred at 0° C. for 1 hour and allowed to warm up to RT over an hour then stirred at RT for 1 hour. The THF was evaporated and a mixture of ethyl acetate (80 mL) and hexane (120 mL) was added. This mixture stirred for 2 hours and filtered. The precipitate was washed with a mixture of ethyl acetate (20 mL) and hexane (180 mL) and the filtrate evaporated. The residue was purified by column chromatography, eluting with 1:20 to 1:10 ethyl acetate:hexanes, to afford the title compound (65.5 g).

Aufarbeitung

  1. temperatureto warm up to RT over an hour
  2. stirringthen stirred at RT for 1 hour
  3. customThe THF was evaporated
  4. additiona mixture of ethyl acetate (80 mL) and hexane (120 mL)
  5. additionwas added
  6. stirringThis mixture stirred for 2 hours
  7. filtrationfiltered
  8. washThe precipitate was washed with a mixture of ethyl acetate (20 mL) and hexane (180 mL)
  9. customthe filtrate evaporated
  10. customThe residue was purified by column chromatography
  11. washeluting with 1:20 to 1:10 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-07ead5c5453846848e8a567d3f76184a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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