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

HRID 1948590ノート

反応式

HRID 1948590 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7519Anisole溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-038af9659262481b8affa70768704d42
出典データセット
uspto-grants-2013_03
特許番号
US08399503B2

反応ノート

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