Potassium Hydroxide → (R)-(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 38989

Reaction equation

HRID 38989 reaction equation
C([O:3][C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][C@@H:13]1[CH2:15][O:14]1)=O.[OH-].[K+]>O1CCOCC1>[Br:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][CH2:12][C@@H:13]([CH2:15][OH:14])[O:3][C:4]=2[CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 866529425-Bromo-2-[(2S)-oxiran-2-ylmethoxy]phenyl formate

Product 1

HCID 66879096(R)-(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanolYield 57.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-bromo-2-[(2S)-oxiran-2-ylmethoxy]phenyl formate (8.5 g, 31 mmol) was dissolved in dioxane. At 0° C., KOH (10%) was added. The mixture was stirred in rt for 1 h and 30 min and was then concentrated. Water was added. Aqueous HCl (1 N) was added to neutralize and the solution was then extracted with EtOAc (3×75 ml). The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the crude title compound (4.4 g). MS m/z (rel. intensity, 70 eV) 245 (M+, 97) 244 (M+, bp), 189 (48), 188 (50) 70 (39).

Workup

  1. concentrationwas then concentrated
  2. additionWater was added
  3. additionAqueous HCl (1 N) was added
  4. extractionthe solution was then extracted with EtOAc (3×75 ml)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customPurification on flash column chromatography (isooctane/EtOAc)

Sources & evidence

ORD record
ord-61f24cfec60f48afa1900c5526d9dd01
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

Loading…