Triphenylphosphine → Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate

HRID 20507

Reaktionsgleichung

Reaktionsgleichung von HRID 20507
[Si:1]([O:8][CH2:9][C@H:10]([OH:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18].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>[Si:1]([O:8][CH2:9][C@H:10]([CH3:11])[O:12][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoateHCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol

Produkt 1

HCID 59127165Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoateAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(2R)-1-{[tert-Butyl(dimethyl)silyl]oxy}propan-2-ol (3.31 g, 17.4 mmol) was added to a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (3.00 g, 11.6 mmol) in THF (50 mL) at 0° C. followed by addition of triphenylphosphine (4.57 g, 17.4 mmol) then DIAD (3.43 mL, 17.4 mmol) and the reaction was warmed to RT and stirred for 16 h. The reaction was quenched with water (100 mL) and diethyl ether (400 mL) and the organic layer was separated then dried (MgSO4) and evaporated. Purification by column chromatography, eluting with 1:15 to 1:5 ethyl acetate:hexane, afforded the title compound as a colourless oil (4.00 g, 80%).

Aufarbeitung

  1. customThe reaction was quenched with water (100 mL) and diethyl ether (400 mL)
  2. customthe organic layer was separated
  3. dry with materialthen dried (MgSO4)
  4. customevaporated
  5. customPurification by column chromatography
  6. washeluting with 1:15 to 1:5 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8c2a0ba8e4894774af4fbc85a229ffbc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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