Hydrochloric Acid → Spiro(4.5)decane-6-carbaldehyde

HRID 1594155노트

반응식

HRID 1594155 반응식
C(OP(C[N+]#[C-])(=O)[O:5][CH2:6][CH3:7])C.C([Li])CCC.[CH2:17]1[C:21]2(C[CH2:25][CH2:24][CH2:23][C:22]2=O)[CH2:20][CH2:19][CH2:18]1.Cl>C(OCC)C.CCCCCC.O>[CH2:20]1[C:21]2([CH2:22][CH2:23][CH2:24][CH2:25][CH:7]2[CH:6]=[O:5])[CH2:17][CH2:18][CH2:19]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 290662Spiro(4.5)decan-6-oneHCID 2734699Diethyl (isocyanomethyl)phosphonateHCID 178418339Butyllithium

생성물 1

HCID 12610319Spiro(4.5)decane-6-carbaldehyde

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

A solution of diethyl(isocyanomethyl)phosphonate (410 μL) in diethyl ether (5 mL) was cooled to −78° C. in nitrogen atmosphere. After addition of 1.54M n-butyl lithium solution in hexane (1.7 mL) to the reaction mixture at −78° C., the temperature was raised to 0° C. and stirred for 15 minutes. To the resulting solution spiro[4.5]decane-6-one (300 mg) was added at 0° C., and the temperature was raised to room temperature under stirring. An hour thereafter, conc. hydrochloric acid (5 mL) was added to the reaction mixture at room temperature, followed by further 10 hours' stirring. The resulting solution was diluted with water and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, and from which the solvent was distilled off to provide the title compound in crude, unpurified form, as a colorless oily substance.

후처리

  1. temperaturethe temperature was raised to room temperature
  2. stirringunder stirring
  3. waitfollowed by further 10 hours
  4. stirring' stirring
  5. extractionextracted with diethyl ether
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. distillationfrom which the solvent was distilled off

출처 및 근거

ORD 기록
ord-8e8a1ddbcfab428684c7bdb8498c04e9
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07300947B2

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