Sodium Hydroxide → 5-Phenyl-2-Thiophenecarboxylic Acid

HRID 896460

반응식

HRID 896460 반응식
[C:1]1([C:7]2[S:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+].[OH-].[Na+]>C1COCC1.CC(O)(C)C.O>[C:1]1([C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 1770535-Phenylthiophene-2-carbaldehydeHCID 516951Monobasic potassium phosphateHCID 23668197Sodium Chlorite

생성물 1

HCID 7364945-Phenyl-2-Thiophenecarboxylic Acid수율 51%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6386tert-Butanol용매HCID 8028Tetrahydrofuran용매

실험 절차

The product of Step 3a (750 mg, 4 mmol) is dissolved in a mixture of THF, t-BuOH, and water (2:1:1, 60 mL). KH2PO4 (1.36 g, 10 mmol) is added followed by NaClO2 (900 mg, 10 mmol). The mixture is stirred at rt for 5 days. Aqueous NaOH (2M, 10 mL) is added, and a majority of the organic solvents are removed in vacuo yielding an aqueous suspension. This suspension is diluted with water and washed three times with CH2Cl2. The aqueous layer is acidified to pH<6 with 25% H2SO4 and the product is extracted three times with CH2Cl2. The combined organic washes are dried over Na2SO4, filtered and concentrated in vacuo to yield 5-phenylthiophene-2-carboxylic acid (417 mg, 51%). MS for C11H8O2S (ESI) (M−H)− m/z 203.

후처리

  1. customa majority of the organic solvents are removed in vacuo
  2. customyielding an aqueous suspension
  3. washwashed three times with CH2Cl2
  4. extractionthe product is extracted three times with CH2Cl2
  5. dry with materialThe combined organic washes are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8d9341c200af4a11b7564baeaf984503
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919359B2

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