Diisobutylaluminumhydride → (3-Amino-5-ethoxy-4-iodo-phenyl)-methanol

HRID 502368노트

반응식

HRID 502368 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:7]([I:13])=[C:6]([NH2:14])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[NH2:14][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:7]=1[I:13]

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 684595793-Amino-5-ethoxy-4-iodo-benzoic acid methyl ester

생성물 1

HCID 68454929(3-Amino-5-ethoxy-4-iodo-phenyl)-methanol수율 34.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-amino-5-ethoxy-4-iodo-benzoic acid methyl ester (0.18 g, 0.56 mmol) in THF (5 mL) at 0° C. under Ar was slowly added diisobutylaluminium hydride (2.8 mL, 2.80 mmol, 1 M solution in THF) over a time period of 30 min, the cooling bath removed on completion of addition and the reaction allowed to reach rt. After 2 h, the excess hydride was quenched by cautious addition of a sat. solution of potassium sodium tartrate (50 mL). The solidified mixture was extracted with hot THF, the combined organic phases concentrated by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1) providing 0.056 g (34%) of the title compound.

후처리

  1. customat 0° C.
  2. customover a time period of 30 min
  3. customthe cooling bath removed on completion of addition
  4. customto reach rt
  5. customthe excess hydride was quenched by cautious addition of a sat. solution of potassium sodium tartrate (50 mL)
  6. extractionThe solidified mixture was extracted with hot THF
  7. concentrationthe combined organic phases concentrated by evaporation under reduced pressure
  8. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-1dd62d4f5a7d46f0acb6c13f4404ed69
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772253B2

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