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Sodium Carbonate → 7-Methoxybenzo[b]thiophene-4-carbaldehyde

HRID 2060876
Notes
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Reaction equation

HRID 2060876 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[C:16]2[S:15][CH:14]=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.[C:17]([O-])([O-])=[O:18].[Na+].[Na+]>CN(C=O)C>[CH3:6][O:7][C:8]1[C:16]2[S:15][CH:14]=[CH:13][C:12]=2[C:11]([CH:17]=[O:18])=[CH:10][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 110842177-Methoxybenzo[b]thiophene

Product 1

HCID 106792907-Methoxybenzo[b]thiophene-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorous oxychloride (0.518 g, 17.7 mmol) was added to DMF (1.04 mL) under argon at rt. After 30 min 7-methoxybenzothiophene (0.5 g, 3.04 mmol) was added and the reaction was heated to 100° C. for 3.5 h. The reaction was cooled to rt and poured into a saturated Na2CO3 solution, extracted with ether (100 mL) and the organic phase dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=3.34 min; m/z (ES+)=193.2 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to rt
  2. extractionextracted with ether (100 mL)
  3. dry with materialthe organic phase dried (MgSO4)
  4. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-acb87c1c32f9409b84c5f1e61d38fb0e
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08278442B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes