DL-2-Phenoxypropionic acid → 3-(4-Benzyloxy-3-methoxyphenyl)-3-hydroxy-2-methyl-2-phenoxypropionic Acid

HRID 1393403

Reaktionsgleichung

Reaktionsgleichung von HRID 1393403
[Li+].CC([N-]C(C)C)C.[O:9]([CH:16]([CH3:20])[C:17]([OH:19])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:21]([O:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][C:30]=1[O:37][CH3:38])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1CCCCC1.C1COCC1>[CH2:21]([O:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]([OH:34])[C:16]([CH3:20])([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17]([OH:19])=[O:18])=[CH:31][C:30]=1[O:37][CH3:38])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

6

Edukt 3

HCID 13658DL-2-Phenoxypropionic acidHCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 223400103-(4-Benzyloxy-3-methoxyphenyl)-3-hydroxy-2-methyl-2-phenoxypropionic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

A stirred solution of LDA in cyclohexane (1.5 M) was cooled to −20° C., to which a solution of 2-phenoxypropionic acid (10 g, 60.2 mmol) in THF (80.3 mL) was slowly added, keeping the temperature below −10° C. The resulting dianion solution was stirred for 15 min, then a solution of 4-benzyloxy-3-methoxybenzaldehyde (14.58 g, 60.2 mmol) in THF (80.3 mL) was added over 1 h, maintaining temperature below −10° C. Fifteen minutes after completion of aldehyde addition, the reaction mixture was poured onto ice water (200 mL), and extracted using 1:2 Et2O:hexane (500 mL). The aqueous layer was isolated, extracted again with 1:2 Et2O:hexane (240 mL), then acidified with concentrated HCl until pH=3. The product acid was extracted into EtOAc (2×165 mL), which was dried over Na2SO4 and concentrated to an orange paste (16.5 g crude, 67%): MS (EI) 426.2 (M+NH4)+, 407.2 (M−H)−.

Aufarbeitung

  1. additionwas slowly added
  2. customthe temperature below −10° C
  3. temperaturemaintaining temperature below −10° C
  4. additionthe reaction mixture was poured onto ice water (200 mL)
  5. extractionextracted
  6. customThe aqueous layer was isolated
  7. extractionextracted again with 1:2 Et2O
  8. extractionThe product acid was extracted into EtOAc (2×165 mL), which
  9. dry with materialwas dried over Na2SO4
  10. concentrationconcentrated to an orange paste (16.5 g crude, 67%)

Quellen und Nachweise

ORD-Eintrag
ord-aea33518253443a1bb23869143232761
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345070B2

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