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

HRID 402765ノート

反応式

HRID 402765 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-13f7f37a386f4f338cfb418d935bb65f
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

反応ノート

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