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

HRID 1431006
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HRID 1431006 반응식
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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-180298702bf340e8bdb7da94082b2188
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08940927B2

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