Hydrochloric Acid → 4-(1-Hydroxy-4-iodobutyl)-alpha,alpha-dimethylphenylacetic acid

HRID 1082107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1082107
[I:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:6].[BH4-].[Na+].Cl>CO>[OH:6][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)[CH2:4][CH2:3][CH2:2][I:1]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 113143824-(4Iodo-1-oxobutyl)-alpha,alpha-dimethylphenylacetic acid

Produkt 1

HCID 222227064-(1-Hydroxy-4-iodobutyl)-alpha,alpha-dimethylphenylacetic acidAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 50 mg of 4-(4-iodo-1-oxobutyl)-α,α-dimethylphenylacetic acid, prepared in accordance with Example 3, in 3 mL of methanol was added 50 mg of NaBH4. The mixture was stirred for 30 minutes, acidified with 2N HCl, and the methanol removed in vacuo. The concentrate was extracted with EtOAc. The organics were dried over Na2SO4, filtered, and concentrated to afford 40 mg of 4-(1-hydroxy-4-iodobutyl)-α,α-dimethylphenylacetic acid.

Aufarbeitung

  1. customthe methanol removed in vacuo
  2. extractionThe concentrate was extracted with EtOAc
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-477fdf65dc504d5caaa23f393427850e
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589487

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