Potassium Hydroxide → HCID 54264423, compound

HRID 1709972Notes

Reaction equation

HRID 1709972 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([CH:7]=O)=[C:5]([OH:13])[CH:4]=1.[OH-].[K+].[CH3:16][O:17][C:18](=[O:25])[CH2:19][CH2:20][C:21](=[O:24])[CH2:22]Br>C(O)C.O>[CH3:16][O:17][C:18](=[O:25])[CH2:19][CH2:20][C:21]([C:22]1[O:13][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:10]([O:11][CH3:12])=[CH:9][C:6]=2[CH:7]=1)=[O:24]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 9855825Methyl 5-bromo-4-oxopentanoateHCID 109869082-Hydroxy-4,5-dimethoxybenzaldehyde

Product 1

HCID 54264423HCID 54264423, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred suspension of 4,5-dimethoxy-2-hydroxy-benzaldehyde (9.3 g) in dry ethanol (90 ml) under nitrogen was added slowly a solution of potassium hydroxide (3.14 g) in dry ethanol (60 ml). The resulting solution was stirred for 20 minutes, then 5-bromo-4-oxo-pentanoic acid methyl ester (10.65 g) was added slowly. The mixture was stirred for 24 hours, then diluted slowly with water (900 ml). The precipitated solid was filtered off, washed with water, dried under vacuum and crystallized from acetone-ether to give 4-(5,6-dimethoxy-benzo[b]furan-2-yl)-4-oxo-butanoic acid methyl ester (4.78 g).

Workup

  1. stirringThe mixture was stirred for 24 hours
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water
  4. customdried under vacuum
  5. customcrystallized from acetone-ether

Sources & evidence

ORD record
ord-a3540c162f404b0b9be91c2ed60033c2
Source dataset
uspto-grants-1990_08
Patent number
US04952571

Reaction notes

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