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Sodium Thiosulfate → [4-(2-Pyrimidinyl)phenyl]-2-propynal

HRID 2416543
ノート
印刷プレビュー

反応式

HRID 2416543 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH2:37][OH:38])=[CH:31][CH:30]=1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCl>[N:23]1[CH:28]=[CH:27][CH:26]=[N:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH:37]=[O:38])=[CH:31][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 226311353-[4-(2-Pyrimidinyl)phenyl]-2-propyn-1-ol

生成物 1

HCID 22630855[4-(2-Pyrimidinyl)phenyl]-2-propynal収率 89.3%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A mixture of the Dess-Martin reagent (1.59 g, 3.75 mmol) and 3-[4-(2-pyrimidinyl)phenyl]-2-propyn-1-ol (525 mg, 2.50 mmol, prepared as described in Reference Example 239) in dichloromethane (15 mL) was stirred at room temperature for 30 min. Aqueous 10% Na2S2O3 (25 mL) and aq. sat. NaHCO3 (15 mL) were added, the mixture was stirred for 5 min, the layers were separated, and the aqueous layer was extracted with dichloromethane (10 mL). The combined organic layers were dried (MgSO4) and concentrated to provide 465 mg (89%) of the title compound as a yellow solid. MS 209 (M+H)+.

後処理

  1. stirringthe mixture was stirred for 5 min
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (10 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e1ee9ea0a3c44a5399c1af8e67481c1e
出典データセット
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06825170B2

反応ノート

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