Imidazole → Ethyl 17-iodoheptadecanoate

HRID 1367725ノート

反応式

HRID 1367725 の反応式
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:47]C1C=CC(CCCCCCCCCCCCCCCCCCO)=CC=1>C(Cl)Cl.C1C=CC=CC=1>[I:47][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

参加物

7

反応物 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 1165580418-(p-Iodophenyl)octadecanolHCID 21833404Ethyl 17-hydroxy-heptadecanoate

生成物 1

HCID 86625642Ethyl 17-iodoheptadecanoate収率 90%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Ethyl 17-hydroxy-heptadecanoate 79 (264 mg, 0.84 mmol), Ph3P (262 mg, 1 mmol) and imidazole (94 mg, 1.39 mmol) were dissolved in the mixture of CH2Cl2 (3 ml) and benzene (3 ml) and cooled to 0° C. Solid 12 (254 mg, 1 mmol) was added and the reaction mixture was stirred at 0° C. for 40 min. The reaction mixture was quenched by addition of MeOH (0.5 ml), diluted with EtOAc and washed with the aqueous NaHCO3—Na2S2O3 solution, dried over Na2SO4 and evaporated. Chromatography in hexane-EtOAc (97:3) afforded the product 80 (321 mg, 90%).

後処理

  1. customThe reaction mixture was quenched by addition of MeOH (0.5 ml)
  2. additiondiluted with EtOAc
  3. washwashed with the aqueous NaHCO3—Na2S2O3 solution
  4. dry with materialdried over Na2SO4
  5. customevaporated

出典と根拠

ORDレコード
ord-4b8fe358cf8f479d9f84c425e6d4116d
出典データセット
uspto-grants-2011_02
特許番号
US07893286B2

反応ノート

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