Acetone → 1-(Benzo[b]thien-5-yl)but-1-en-3-one

HRID 978313Notes

Reaction equation

HRID 978313 reaction equation
[OH-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH:12]=O)[CH:10]=[CH:11][C:4]1=2.[CH3:14][C:15]([CH3:17])=[O:16]>O>[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH:12]=[CH:14][C:15](=[O:16])[CH3:17])[CH:10]=[CH:11][C:4]1=2

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 139097Benzo(b)thiophene-5-carboxaldehyde

Product 1

HCID 573189081-(Benzo[b]thien-5-yl)but-1-en-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An aqueous solution of 10% sodium hydroxide (1 ml) was added dropwise to a solution of benzo[b]thiophene-5-carboxaldehyde (7.0 g) in acetone (15 ml) and water (5 ml), the temperature of the reaction mixture being maintained below 30° C. during the addition. On completion of the reaction (ca 3 hrs) the mixture was poured into water. The dried (MgSO4) dichloromethane extract was evaporated to give 1-(benzo[b]thien-5-yl)but-1-en-3-one as a yellow solid, mp 75° C.

Workup

  1. temperaturethe temperature of the reaction mixture being maintained below 30° C. during the addition
  2. customOn completion of the reaction (ca 3 hrs) the mixture
  3. dry with materialThe dried (MgSO4) dichloromethane
  4. extractionextract
  5. customwas evaporated

Sources & evidence

ORD record
ord-918d694373874c35bb83fb656e020cf0
Source dataset
uspto-grants-1987_05
Patent number
US04664693

Reaction notes

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