Diisobutylaluminum hydride → 4-Iodo-2-methoxybenzyl alcohol

HRID 514534

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HRID 514534 반응식
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-]>C1COCC1>[I:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[C:4]([O:12][CH3:13])[CH:3]=1

참가 물질

5

반응물 3

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 22619468Benzoic acid, 4-iodo-2-methoxy-, methyl ester

생성물 1

HCID 187797924-Iodo-2-methoxybenzyl alcohol수율 31.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of methyl 4-iodo-2-methoxybenzoate (840 mg, 2.88 mmol) in THF was purged with nitrogen and cooled to −78° C. DIBALH (6 mL, 5.75 mmol, 1M in toluene) was added slowly. The mixture was then stirred at the same temperature for an hour. Saturated aqueous NH4Cl solution was added, followed by extraction with ethyl acetate twice. The organic phase was then washed with brine and dried with anhydrous Na2SO4. Solvent was removed and the resulting residue purified by flash column chromatograph to give 237 mg of the title compound (31%). 1H NMR (400 MHz, CDCl3): δ 2.17 (1H, s), 3.84 (3H, s), 4.62 (2H, d, J=4.0 Hz), 7.01 (1H, d, J=7.6 Hz), 7.18 (1H, s), 7.29 (1H, d, J=8.0 Hz).

후처리

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe organic phase was then washed with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customSolvent was removed
  5. customthe resulting residue purified by flash column chromatograph

출처 및 근거

ORD 기록
ord-1d531f9b47474f1b86623a248e6a9531
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107916B2

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