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

HRID 1633516Notes

Reaction equation

HRID 1633516 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-8e0b95a68aa849e9a4916b8e8f1ad0bb
Source dataset
uspto-grants-2003_01
Patent number
US06503917B1

Reaction notes

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