2-Hydroxyphenyltriphenylphosphonium bromide → Methyl E-4-{7-cyano-3-[2-(2-hydroxyphenyl)vinyl]heptyl}benzoate

HRID 1927427ノート

反応式

HRID 1927427 の反応式
[CH2:1]([Li])CCC.[Br-].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([CH:52]=O)[CH2:40][CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=1)#[N:34]>CCCCCC.C1COCC1>[C:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39](/[CH:52]=[CH:1]/[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[OH:7])[CH2:40][CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=1)#[N:34]

参加物

6

反応物 3

HCID 573460052-Hydroxyphenyltriphenylphosphonium bromideHCID 57831357Methyl 4-(7-cyano-3-formylheptyl)benzoateHCID 178418339Butyllithium

生成物 1

HCID 57831335Methyl E-4-{7-cyano-3-[2-(2-hydroxyphenyl)vinyl]heptyl}benzoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

9.07 ml (14.52 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added dropwise to a suspension of 3.26 g (7.26 mmol) of 2-hydroxyphenyltriphenylphosphonium bromide in 40 ml of dry THF at 0° C., and the mixture is stirred for 5 minutes. Then, at this temperature, a solution of 1.49 g (5.19 mmol) of methyl 4-(7-cyano-3-formylheptyl)benzoate in 10 ml of dry THF is slowly added dropwise. The reaction mixture is stirred at 0° C. for 10 minutes. The cooling is then removed, and the reaction solution is stirred at room temperature for 10 minutes and then mixed with silica gel and concentrated to dryness. The resulting residue is purified directly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:2→1:5). 1.71 g (75% purity, 3.40 mmol, 65% of theory) of an oil are obtained.

後処理

  1. stirringThe reaction mixture is stirred at 0° C. for 10 minutes
  2. customThe cooling is then removed
  3. stirringthe reaction solution is stirred at room temperature for 10 minutes
  4. additionmixed with silica gel
  5. concentrationconcentrated to dryness
  6. customThe resulting residue is purified directly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:2→1:5)
  7. custom1.71 g (75% purity, 3.40 mmol, 65% of theory) of an oil are obtained

出典と根拠

ORDレコード
ord-f4281a737506442ebcb53343d17249b2
出典データセット
uspto-grants-2012_05
特許番号
US08183271B2

反応ノート

読み込み中…