Triethylamine → 8-Isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decane

HRID 1948590노트

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HRID 1948590 반응식
[C:1]1([C:7]2(C(O)=O)[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:22]([CH2:25]C)CC)C.[N-]=[N+]=[N-].C1([O:36]P(=O)(O)OC2C=CC=CC=2)C=CC=CC=1>C1(OC)C=CC=CC=1>[N:22]([C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][C:10]2([O:11][CH2:12][CH2:13][O:14]2)[CH2:15][CH2:16]1)=[C:25]=[O:36]

참가 물질

5

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HCID 8471TriethylamineHCID 122867028-Phenyl-1,4-dioxaspiro[4.5]decane-8-carboxylic acidHCID 66782931Phosphoric acid diphenylester azide

생성물 1

HCID 125955658-Isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decane

시약·촉매·용매 1

HCID 7519Anisole용매

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온도
0 °C

실험 절차

8-phenyl-1,4-dioxaspiro[4.5]decane-8-carboxylic acid (3 g, 11.5 mmole) was added to anisole (30 ml). The resultant suspension was cooled to a temperature of 0° C. in an ice-salt bath and triethylamine (2.25 ml, 16 mmole) was added. A clear solution was formed, which was stirred for a further 15 minutes at 0° C. Phosphoric acid diphenyl ester azide (2.5 ml, 11.5 mmole) was then added to the mixture within 5 minutes. The reaction mixture was stirred for 20 minutes at 0° C., left to cool to RT within a further 20 minutes, and was then heated in an oil bath for 2 hours at 100° C. (bath temperature). The reaction mixture was worked up by distilling off the anisole under an oil pump vacuum. The chromatographic purification was carried out on silica gel with toluene. The desired product was obtained as a crystalline solid with a melting point of 38°-41° C. in a yield of 2.7 g (91%).

후처리

  1. customA clear solution was formed
  2. stirringThe reaction mixture was stirred for 20 minutes at 0° C.
  3. waitleft
  4. temperatureto cool to RT within a further 20 minutes
  5. temperaturewas then heated in an oil bath for 2 hours at 100° C. (bath temperature)
  6. distillationby distilling off the anisole under an oil pump vacuum
  7. customThe chromatographic purification

출처 및 근거

ORD 기록
ord-038af9659262481b8affa70768704d42
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399503B2

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