Hydrochloric Acid → 7-Hydroxybenzo[b]thiophene-4-carbaldehyde

HRID 2060877Notes

Reaction equation

HRID 2060877 reaction equation
C[O:2][C:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6]([CH:12]=[O:13])=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].Cl.C(N(C(S)C)CC)C.Cl>CN(C=O)C>[OH:2][C:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6]([CH:12]=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 106792907-Methoxybenzo[b]thiophene-4-carbaldehydeHCID 236176041-(Diethylamino)ethanethiol;hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 594013507-Hydroxybenzo[b]thiophene-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Methoxybenzo[b]thiophene-4-carbaldehyde (Preparation 68) (844 mg, 4.39 mmol) was added to a suspension of potassium tert-butoxide (1.5 g, 14.0 mmol) and diethylaminoethanethiol hydrochloride (1.12 g, 6.58 mmol) in DMF (22 mL). The mixture was refluxed for 1 h. After cooling the mixture was acidified to pH 1 with 1N HCl and the aqueous phase extracted with EtOAc. The organic phase was washed with water, brine and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=2.59 min; m/z (ES+)=178.2 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperatureAfter cooling the mixture
  3. extractionthe aqueous phase extracted with EtOAc
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-1707446d7d3440a5860aacb6ff1b041d
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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