Methanol → 3-(1,3-Benzodioxol-5-yl)-1-(2-hydroxyphenyl)-2-propen-1-one

HRID 1934503Notes

Reaction equation

HRID 1934503 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH2:11]1[O:21][C:20]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=2[O:12]1.C[O-:23].[Na+].CO>C(OC)(OC)OC>[OH:23][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:3](=[O:4])[CH:2]=[CH:16][C:15]1[CH:18]=[CH:19][C:20]2[O:21][CH2:11][O:12][C:13]=2[CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8438PiperonalHCID 68490alpha-HydroxyacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 2617033-(1,3-Benzodioxol-5-yl)-1-(2-hydroxyphenyl)-2-propen-1-one

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

A mixture of 2-hydroxyacetophenone on Wang resin (2.0 g, 1.76 mmol) was swelled in trimethyl orthoformate (20 mL) for 10 min. 3,4-Methylenedioxybenzaldehyde (6.0 mmol) was added and 25% NaOMe in MeOH (0.86 g, 4.0 mmol) was added to the mixture dropwise over 30 min. The mixture was then stirred for an additional 0.5 h. The resin was filtered and washed with alternating MeOH and CH2Cl2 (×5) and dried under high vacuum overnight to give 2.23 g of 1-(2-hydroxyphenyl)-3-(3,4-methylenedioxyphenyl)-2-propen-1-one on Wang resin.

Workup

  1. filtrationThe resin was filtered
  2. washwashed with alternating MeOH and CH2Cl2 (×5)
  3. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-4ccae9e757994a729abccd5c8d856d2f
Source dataset
uspto-grants-2002_05
Patent number
US06384057B1

Reaction notes

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