Sodium borohydride → {4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}methanol

HRID 2194861ノート

反応式

HRID 2194861 の反応式
[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[BH4-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 579560774-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]benzaldehyde

生成物 1

HCID 67447508{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}methanol

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a solution of the aldehyde from Step 2 (1 eq.) in a mixture of THF/MeOH (2/1, 0.21M) was added portion wise sodium borohydride (1.5 eq.). The mixture was stiffed 3 h at room temperature, quenched slowly with 1N HCl and finally concentrated in vacuo. The residual aqueous phase was extracted with diethylether twice. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Stirring the residue in 10% Et2O/Hex for 4 h followed by filtration afforded the desired alcohol as a white crystalline solid.

後処理

  1. customquenched slowly with 1N HCl
  2. concentrationfinally concentrated in vacuo
  3. extractionThe residual aqueous phase was extracted with diethylether twice
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationfollowed by filtration

出典と根拠

ORDレコード
ord-062e222120974d5cb3fbde44196a10f5
出典データセット
uspto-grants-2012_12
特許番号
US08334308B2

反応ノート

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