8-Bromochroman-4-carboxylic acid → (8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol

HRID 2173255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173255
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[C:12](O)=[O:13]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[CH2:12][OH:13]

Komponenten

3

Edukt 1

HCID 675164228-Bromochroman-4-carboxylic acid

Produkt 1

HCID 67516017(8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 8-bromo-3,4-dihydro-2H-chromene-4-carboxylic acid (3.1 g, 12 mmol) in 50 mL THF was added BH3 (24 mL, 24 mmol, C=1.0 M in THF) dropwise at 0° C. The mixture was stirred at 0° C. for 2-3 hours before quenched with MeOH (8 mL), and evaporated. The residue was partitioned between water and EtOAc. The organic phase was washed with 3N HCl, saturated Na2CO3, and brine, dried over anhydrous Na2SO4 and concentrated to afford (8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol.

Aufarbeitung

  1. custombefore quenched with MeOH (8 mL)
  2. customevaporated
  3. customThe residue was partitioned between water and EtOAc
  4. washThe organic phase was washed with 3N HCl, saturated Na2CO3, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-765f330068a042cabb7d7196779be9ac
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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