Methanol → 2-(1,3-Dioxaindan-5-yl)ethan-1-ol

HRID 456586

Reaktionsgleichung

Reaktionsgleichung von HRID 456586
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11](O)=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.CO>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][OH:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 76115Benzo-1,3-dioxole-5-acetic acid

Produkt 1

HCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-olAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of benzo[1,3]dioxol-5-yl-acetic acid (2.5 g, 13.9 mmol) in tetrahydrofuran (15 ml) under argon at −10° C. was treated dropwise with borane-dimethylsulfide complex (1.45 ml, 15.3 mmol). The mixture was stirred at ambient temperature for 1.5 hours (CAUTION—exothermic reaction). The orange solution was cooled to ˜5° C. (ice bath) and methanol (1.4 ml) was added. After 0.5 hour at room temperature, the mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried and evaporated to give a yellow oil (1.95 g, 84%).

Aufarbeitung

  1. custom(CAUTION—exothermic reaction)
  2. additionwas added
  3. waitAfter 0.5 hour at room temperature
  4. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. extractionThe organic extract
  6. customwas dried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dadc8725412f43c9a0455c7f5e60521b
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186730B2

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