Hydrochloric Acid → HCID 23035258, compound

HRID 1651632Notes

Reaction equation

HRID 1651632 reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:6]2[S:7][C:8]([C:10]#N)=[CH:9][C:5]=2[CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C[OH:27].Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:6]2[S:7][C:8]([CH:10]=[O:27])=[CH:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21225700DiisobutylaluminumhydrideHCID 23050245HCID 23050245, compound

Product 1

HCID 23035258HCID 23035258, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-5 °C

Procedure

5,6-Dimethoxy-benzo[b]thiophene-2-carbonitrile (2.0 g) was suspended in dry toluene (40 ml) under an atmosphere of nitrogen. The reaction mixture was cooled to -5° C. and treated dropwise with a solution of diisobutylaluminium hydride in toluene (1.5M, 13 ml). After 30 minutes the solution was treated with methanol (5 ml) then poured into hydrochloric acid (1M, 200 ml) and stirred for 15 minutes. The resultant solution was extracted into dichloromethane (4×100 ml) then the organic extracts were combined, washed with brine, dried over magnesium sulphate and evaporated to dryness. The orange residue (1.6 g) was crystallised from dichloromethane:ether to give 5,6-dimethoxy-benzo[b]thiophene-2-carboxaldehyde as a white solid, m.p. 155°-156° C.

Workup

  1. extractionThe resultant solution was extracted into dichloromethane (4×100 ml)
  2. washwashed with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness
  5. customThe orange residue (1.6 g) was crystallised from dichloromethane

Sources & evidence

ORD record
ord-9a54500a122144afb2a7e5679601853e
Source dataset
uspto-grants-1990_05
Patent number
US04929636

Reaction notes

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