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

HRID 427119노트

반응식

HRID 427119 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

HCID 14658350rac. 4-Benzyloxy-3-methylbutanal

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-246f051f759844f2b0154aefd75a2398
출처 데이터셋
uspto-grants-1979_10
특허 번호
US04172958

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