Diisobutylaluminum hydride → (2-(Benzyloxy)-4-iodophenyl)methanol

HRID 2387875

Reaktionsgleichung

Reaktionsgleichung von HRID 2387875
CC(C[AlH]CC(C)C)C.[CH2:10]([O:17][C:18]1[CH:27]=[C:26]([I:28])[CH:25]=[CH:24][C:19]=1[C:20](OC)=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([O:17][C:18]1[CH:27]=[C:26]([I:28])[CH:25]=[CH:24][C:19]=1[CH2:20][OH:21])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydride2×HCID 66990993Methyl 2-(benzyloxy)-4-iodobenzoate

Produkt 1

HCID 68417547(2-(Benzyloxy)-4-iodophenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of DIBAL-H (179 mL, 1M) was added to a solution of the product from step (i) (26.4 g) in THF (400 ml) at rt. The mixture was stirred for 3 h then a further 0 ml of DIBAL-H was added and stirred for a further 1 h. The mixture was quenched carefully with EtOAc and then with 2M aq HCl. The mixture was partitioned between ether/2M HCl, the organics were separated, washed with water, dried and evaporated under reduced pressure. The residue was triturated with isohexane and filtered to give the subtitle compound as a solid, 21 g.

Aufarbeitung

  1. stirringstirred for a further 1 h
  2. customThe mixture was quenched carefully with EtOAc
  3. customThe mixture was partitioned between ether/2M HCl
  4. customthe organics were separated
  5. washwashed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with isohexane
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-3794eed59fbd4618b353fd1c0fcce18b
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268990B2

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