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

HRID 38989노트

반응식

HRID 38989 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-61f24cfec60f48afa1900c5526d9dd01
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524766B2

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