Benzyl Bromide → 2-(Benzyloxy)-4,6-di-tert-butylbenzaldehyde

HRID 1173332ノート

反応式

HRID 1173332 の反応式
[C:1]([C:5]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[C:9]([OH:17])[C:6]=1[CH:7]=[O:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:17][C:9]1[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[CH:7]=[O:8])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 128155852,4-Di-tert-butyl-6-hydroxybenzaldehyde

生成物 1

HCID 866011722-(Benzyloxy)-4,6-di-tert-butylbenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1.17 g (5.0 mmol) of 2,4-di-tert-butyl-6-hydroxybenzaldehyde (from Step A of Example 35) in 10 mL of dry DMF was added 0.25 g (10.4 mmol) of powdered sodium hydride and the resulting mixture was stirred for 30 min under a nitrogen atmosphere. Benzyl bromide (1.0 g, 5.9 mmol) was then added and the resulting mixture was stirred for an additional 3 h. The reaction mixture was then concentrated in vacuo and the residue was partitioned between ether and water. The aqueous layer was re extracted with ether and the organic layers were then combined, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0-10% EtOAc-hexane. Combination of the purified fractions and drying in vacuo afforded the title compound.

後処理

  1. stirringthe resulting mixture was stirred for an additional 3 h
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe residue was partitioned between ether and water
  4. extractionThe aqueous layer was re extracted with ether
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on a silica gel flash chromatography column
  9. washeluted with 0-10% EtOAc-hexane
  10. customCombination of the purified fractions and drying in vacuo

出典と根拠

ORDレコード
ord-421ea27c3f9f489e92a416047c093cc1
出典データセット
uspto-grants-2010_11
特許番号
US07834062B2

反応ノート

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