Sodium borohydride → Methyl thien-2-yl-hydroxyacetate

HRID 1080710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1080710
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8].[BH4-].[Na+]>C(O)C.O>[OH:11][CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 11217486Methyl alpha-oxo-2-thiopheneacetate

Produkt 1

HCID 13682356Methyl thien-2-yl-hydroxyacetateAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 2-thiopheneglyoxylate (1.01 g) in ethanol (20 ml) in an ice bath was added sodium borohydride (0.113 g) in 1 ml of water, and the mixture was stirred for 10 minutes. The reaction was quenched with aqueous acetic acid and the mixture was partitioned between methylene chloride and water. The organic extract was washed with brine, dried (sodium sulfate) and evaporated to give methyl α-hydroxy-2-thienylacetate as an oil (0.903 g).

Aufarbeitung

  1. customThe reaction was quenched with aqueous acetic acid
  2. customthe mixture was partitioned between methylene chloride and water
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-657ee4f9087f4328a004c25ec7dafb83
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05583147

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