Chloride → 4-Azido-7-cyanochroman

HRID 32051ノート

反応式

HRID 32051 の反応式
Cl[CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[N-:14]=[N+:15]=[N-:16].[Na+].C1(C)C=CC=CC=1.[Cl-]>CN(C=O)C>[N:14]([CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1)=[N+:15]=[N-:16]

参加物

6

反応物 4

HCID 312ChlorideHCID 1140TolueneHCID 33557Sodium AzideHCID 18448592HCID 18448592、化合物

生成物 1

HCID 184485894-Azido-7-cyanochroman

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

4-Chloro-7-cyanochroman (Step C) (8.1 g, 42 mmol) was dissolved in dry DMF (90 mL) and NaN3 (4.0 g, 62 mmol) was added and the reaction was heated to 80° C. under N2. After 5 h TLC (SiO2, toluene) showed that no starting chloride was present. The reaction was cooled and partitioned between EtOAc (200 mL) and H2O (150 mL). The organic phase was washed with H2O (2×100 mL) and brine (100 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 15% EtOAc in hexane) to provide the title compound.

後処理

  1. temperatureThe reaction was cooled
  2. custompartitioned between EtOAc (200 mL) and H2O (150 mL)
  3. washThe organic phase was washed with H2O (2×100 mL) and brine (100 mL)
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a residue which
  8. customwas purified by column chromatography (SiO2, 15% EtOAc in hexane)

出典と根拠

ORDレコード
ord-98fd8387528a469cbcf5e2db00cdee14
出典データセット
uspto-grants-2008_09
特許番号
US07425631B2

反応ノート

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