Methyl iodide → 4-Iodo-2-methoxybenzyl alcohol

HRID 1585876ノート

反応式

HRID 1585876 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[C:11]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C>[CH3:11][O:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 187797342-(Hydroxymethyl)-5-iodophenol

生成物 1

HCID 187797924-Iodo-2-methoxybenzyl alcohol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Hydroxy-4-iodo-benzylalcohol from Step 3 (1.0 g, 4.0 mmol), Cs2CO3 (1.3 g, 4.0 mmol) and iodomethane (0.25 mL, 4.0 mmol) were dissolved in DMF and heated to 800 for 1 hour and then stirred at room temperature for 2 hours. The DMF was removed in vacuo and the residue was partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc (2×). The organic layers were combined, washed with H2O and brine, dried (MgSO4), filtered and concentrated to yield an oil. This oil was purified by flash chromatography eluting product with 30% EtOAC/Hexane to give the title compound.

後処理

  1. temperatureheated to 800 for 1 hour
  2. customThe DMF was removed in vacuo
  3. customthe residue was partitioned between H2O and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc (2×)
  5. washwashed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield an oil
  10. customThis oil was purified by flash chromatography
  11. washeluting product with 30% EtOAC/Hexane

出典と根拠

ORDレコード
ord-ce4bbcbf7fd1473b8e7a14eb21f24383
出典データセット
uspto-grants-1999_08
特許番号
US05939439

反応ノート

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