Methanol → Benzofuran-5-yl(pyridin-2-yl)methanol

HRID 2075201

반응식

HRID 2075201 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]=[O:23])=[CH:21][C:16]=2[CH:15]=[CH:14]1.CO>C1COCC1.CCOC(C)=O.O>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[OH:23])=[CH:21][C:16]=2[CH:15]=[CH:14]1

참가 물질

8

반응물 4

HCID 887MethanolHCID 79732-BromopyridineHCID 27738751-Benzofuran-5-carbaldehydeHCID 178418339Butyllithium

생성물 1

HCID 58415302Benzofuran-5-yl(pyridin-2-yl)methanol

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
4 °C

실험 절차

Under argon at −78° C., a mixture of 2-bromopyridine (1.11 g, 7.05 mmol) in THF (30 mL) was dropwise treated with n-BuLi (1.05 equiv. 2.7 mL of 2.5M BuLi in hexanes) over a period of 10 min, and stirred for 10 min. The resulting brown solution was treated dropwise with a solution of benzofuran-5-carbaldehyde (0.937 g, 6.41 mmol) in THF (10 mL) and continued to stir for 15 min at −78° C. The mixture was treated with MeOH (3 mL), followed by H2O (20 mL) and warmed to 4° C. The mixture was treated with EtOAc, the layers separated, and the aqueous layer extracted 1× with EtOAc. The combined organic layers were dried over MgSO4 and evaporated, which resulted in a dark yellow oil which was used without further purification.

후처리

  1. stirringto stir for 15 min at −78° C
  2. customthe layers separated
  3. extractionthe aqueous layer extracted 1× with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated
  6. customwhich resulted in a dark yellow oil which
  7. customwas used without further purification

출처 및 근거

ORD 기록
ord-40979359faeb474794e3d915fc31a186
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

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