Ethyl Acetate → (2-Bromo-5-ethoxy-4-methylphenyl)methanol

HRID 402765노트

반응식

HRID 402765 반응식
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH2:13][CH3:14])=[CH:7][C:3]=1[C:4]([O-])=[O:5].CC(C[AlH]CC(C)C)C.CCOC(C)=O>CCOCC>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH2:13][CH3:14])=[CH:7][C:3]=1[CH2:4][OH:5]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 866768062-Bromo-5-ethoxy-4-methylbenzoate

생성물 1

HCID 66764839(2-Bromo-5-ethoxy-4-methylphenyl)methanol수율 100.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

To a solution of 2-bromo-5-ethoxy-4-methylbenzoate (660 mg, 2.23 mmol) in ether (20 mL) at 0° C. was added DIBAL (5.75 mL, 5.75 mmol, 1 M in toluene). The reaction was stirred at 0° C. for 10 minutes. EtOAc (20 mL) and wet silica gel (˜50 g silica gel and 3 mL of water) were added portion wise at 0° C. The resulting slurry was stirred for ˜15 minutes and was filtered, washed with EtOAc (20 mL). The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with EtOAc/hexanes (20/80) to give the title intermediate (550 mg) as colorless liquid.

후처리

  1. stirringThe resulting slurry was stirred for ˜15 minutes
  2. filtrationwas filtered
  3. washwashed with EtOAc (20 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column
  8. washeluting with EtOAc/hexanes (20/80)

출처 및 근거

ORD 기록
ord-13f7f37a386f4f338cfb418d935bb65f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

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