N-Hydroxyphthalimide → HCID 23353087、化合物

HRID 1768541ノート

反応式

HRID 1768541 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 in the course of 2.5 hours with temperature control (max. 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. After drying and evaporating down, the crude product was purified by chromatography over silica gel. The eluents used were initially dichloromethane/n-hexane and subsequently pure dichloromethane. Yield: 82%; mp.: 85°-88° C. 250-MHz-1H-NMR (in DMSO-d6): δ[ppm]=1.9-2.1 (m, 2H); 2.68 (t, 2H); 4.342 (t, 2H); 7.18 (t, 2H); 7.4-7.6 (m, 2H); 7.85 (s, 4H).

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. customAfter drying
  4. customevaporating down
  5. customthe crude product was purified by chromatography over silica gel

出典と根拠

ORDレコード
ord-bae56c8b8afb463e99e4ecdf278dcb62
出典データセット
uspto-grants-1995_01
特許番号
US05378677

反応ノート

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