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5-Diethylphosphono-2-thiophenecarboxaldehyde → 3-{[5-(Diethoxy-phosphoryl)-thiophen-2-yl]-hydroxy-methyl}-5-isopropoxy-benzoic acid

HRID 1431006
ノート
印刷プレビュー

反応式

HRID 1431006 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:10]=1)[C:5]([OH:7])=[O:6].[Li]CCCC.[CH2:20]([O:22][P:23]([C:28]1[S:29][C:30]([CH:33]=[O:34])=[CH:31][CH:32]=1)(=[O:27])[O:24][CH2:25][CH3:26])[CH3:21]>C1COCC1>[CH2:20]([O:22][P:23]([C:28]1[S:29][C:30]([CH:33]([OH:34])[C:2]2[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:10]=2)[C:5]([OH:7])=[O:6])=[CH:31][CH:32]=1)([O:24][CH2:25][CH3:26])=[O:27])[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 222749525-Diethylphosphono-2-thiophenecarboxaldehydeHCID 532166663-Bromo-5-isopropoxybenzoic acidHCID 178418339Butyllithium

生成物 1

HCID 866595583-{[5-(Diethoxy-phosphoryl)-thiophen-2-yl]-hydroxy-methyl}-5-isopropoxy-benzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 3-bromo-5-isopropoxy-benzoic acid (2.0 g, 8.26 mmol) in THF (30 ml) was added 1.6 M nBuLi (10.6 ml, 16.94 mmol) at −78° C. The reaction was stirred at −78° C. for 1 h and treated with a solution of (5-formyl-thiophen-2-yl)-phosphonic acid diethyl ester (2.5 g, 9.91 mmol) in THF. After stirring at −78° C. for 30 min, the reaction mixture was warmed up to r.t. and quenched by water, diluted with EtOAc. The aqueous layer was separated, acidified with 2N HCl to pH<1, and extracted with EtOAc (3×). The combined EtOAc layers were dried over MgSO4, filtrated, concentrated to give the crude product 3-{[5-(diethoxy-phosphoryl)-thiophen-2-yl]-hydroxy-methyl}-5-isopropoxy-benzoic acid.

後処理

  1. stirringAfter stirring at −78° C. for 30 min
  2. temperaturethe reaction mixture was warmed up to r.t.
  3. customquenched by water
  4. additiondiluted with EtOAc
  5. customThe aqueous layer was separated
  6. extractionextracted with EtOAc (3×)
  7. dry with materialThe combined EtOAc layers were dried over MgSO4
  8. filtrationfiltrated
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-180298702bf340e8bdb7da94082b2188
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08940927B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート