2,3-Dihydroxybutanedioate → (2-Heptyloxy-4-iodophenyl)methanol

HRID 1171431

Reaktionsgleichung

Reaktionsgleichung von HRID 1171431
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:10]=1[C:11](OC)=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(C(C(C([O-])=O)O)O)([O-])=O.[Na].[K]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:10]=1[CH2:11][OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

6

Edukt 4

HCID 38061142,3-DihydroxybutanedioateHCID 5360545SodiumHCID 5462222PotassiumHCID 68767792Methyl 2-heptyloxy-4-iodobenzoate

Produkt 1

HCID 68768142(2-Heptyloxy-4-iodophenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 1M solution of DiBAIH (87.5 ml, 87.5 mmol) is added dropwise to a solution of methyl 2-heptyloxy-4-iodobenzoate obtained in Step a (14 g, 43.7 mmol) in toluene (450 ml), at 0° C. After stirring for 2 hours, a saturated solution of mixed tartrate of sodium and of potassium is added and then the desired product is extracted by addition of ethyl ether. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator. The product is purified by chromatography on a silica column, eluted with a heptane/ethyl acetate 9:1 mixture. After evaporation of the solvents, 13.64 g (90%) of the expected compound are recovered in the form of a yellow oil.

Aufarbeitung

  1. customat 0° C
  2. extractionthe desired product is extracted by addition of ethyl ether
  3. washThe organic phase is washed with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. customThe product is purified by chromatography on a silica column
  8. washeluted with a heptane/ethyl acetate 9:1 mixture
  9. customAfter evaporation of the solvents, 13.64 g (90%) of the expected compound
  10. customare recovered in the form of a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-9580ae30b3c642ae9037d59be00d6108
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829588B2

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