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

HRID 1990832ノート

反応式

HRID 1990832 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-amino-5-ethoxy-4-iodo-benzoic acid methyl ester (0.18 g, 0.56 mmol, 1.0 equiv) in THF (5 mL) at 0° C. under Ar was slowly added diisobutylaluminium hydride (2.8 mL, 2.80 mmol, 5.0 equiv, 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. 1H NMR (250 MHz, CDCl3): δ 1.47 (t, J=7.0 Hz, 3H), 4.08 (q, J=7.0 Hz, 2H), 4.23 (br s, 2H), 4.58 (d, J=6.0 Hz, 2H), 6.23 (s, 1H), 6.42 (s, 1H). MS (EI): 293.0 [M]+.

後処理

  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)

出典と根拠

ORDレコード
ord-dad103d8d7404420b17f2e6d8857af83
出典データセット
uspto-grants-2010_01
特許番号
US07645753B2

反応ノート

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