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

HRID 38989

反応式

HRID 38989 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-61f24cfec60f48afa1900c5526d9dd01
出典データセット
uspto-grants-2013_09
特許番号
US08524766B2

関連ノート

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