N-Hydroxyphthalimide → HCID 23353087、化合物

HRID 2395942ノート

反応式

HRID 2395942 の反応式
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:33][CH2:34][CH2:35][C:36]#[C:37][C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:44][C:41]1[CH:42]=[CH:43][C:38]([C:37]#[C:36][CH2:35][CH2:34][CH2:33][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])=[CH:39][CH:40]=1

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 189879965-(4-Fluorophenyl)-4-pentyn-1-ol

生成物 1

HCID 23353087HCID 23353087、化合物収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

33.4 g (0.205 mol) of N-hydroxyphthalimide and 53.8 g (0.205 mol) of triphenylphosphine were added to a solution of 33.1 g (0.186 mol) of 5-hydroxy-1-(4-fluorophenyl)-1-pentyne in 430 ml of dry tetrahydrofuran. 35.7 g (0.205 mol) of diethyl azodicarboxylate were then added dropwise inthe course of 2.5 hours under temperature control (not more than 40°C.). Stirring was carried out overnight at room temperature, the mixture was evaporated down under reduced pressure and the residue was taken up with 300 ml of dichloromethane. The solution was washed twice with sodium carbonate solution and once with saturated sodium chloride solution. Afterthe solution had been dried and evaporated down, the crude product was purified by chromatography over silica gel. The eluent used was initially dichloromethane/n-hexane and then pure dichloromethane. Yield: 82%; mp.: 85°-88° C.

後処理

  1. customthe mixture was evaporated down under reduced pressure
  2. washThe solution was washed twice with sodium carbonate solution and once with saturated sodium chloride solution
  3. customAfterthe solution had been dried
  4. customevaporated down
  5. customthe crude product was purified by chromatography over silica gel

出典と根拠

ORDレコード
ord-58acb4f3eeaa462bbc01f26bb7c5cb97
出典データセット
uspto-grants-1996_02
特許番号
US05491123

反応ノート

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