Sulfuric Acid → rac. 4-Benzyloxy-3-methylbutanal

HRID 441547ノート

反応式

HRID 441547 の反応式
[CH2:1]([O:8][CH2:9][CH:10]([CH3:14])[CH2:11][C:12]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)=[O:26].[Cl-].[NH4+].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([O:8][CH2:9][CH:10]([CH3:14])[CH2:11][CH:12]=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 1118Sulfuric AcidHCID 8025Ethyl formateHCID 25517Ammonium ChlorideHCID 109762734-(Benzyloxy)-3-methylbutanenitrileHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 14658350rac. 4-Benzyloxy-3-methylbutanal

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒

実験手順

A solution of 5.8 g. (0.0307 mole) of rac. 4-benzyloxy-3-methylbutyronitrile in 290 ml. of hexane was stirred at -65° C. to -70° C. while 22.4 ml. (4.78 g.; 0.0337 mole) of 25% diisobutylaluminum hydride solution in toluene was added dropwise. The resulting solution was stirred at -65° C. to -70° C. for 0.5 hours then at room temperature for 5 hours whereupon 2.8 ml. of ethyl formate was added dropwise. The reaction mixture was then treated with 250 ml. of saturated aqueous ammonium chloride solution. Stirring was continued for 20 minutes at which point 125 ml. of 5% by weight aqueous sulfuric acid was added and stirring was continued for an additional 10 minutes. The organic layer was separated and the aqueous layer was extracted with ether. The organic solutions were combined and processed as in Example 1 giving 4.79 g. (81.3%) of rac. 4-benzyloxy-3-methylbutanal as a yellow oil.

後処理

  1. waitat room temperature for 5 hours whereupon 2.8 ml
  2. additionThe reaction mixture was then treated with 250 ml
  3. stirringStirring
  4. waitwas continued for 20 minutes at which
  5. stirringstirring
  6. waitwas continued for an additional 10 minutes
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with ether

出典と根拠

ORDレコード
ord-3a510482902c4ad789d6367f8b07b533
出典データセット
uspto-grants-1977_08
特許番号
US04041058

反応ノート

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