Methanol → 2-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

HRID 2173120Notes

Reaction equation

HRID 2173120 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH:13]=C.CSC.C[OH:19]>>[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH:13]=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 666465364-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one

Product 1

HCID 772312602-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Procedure

A solution of 4-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one (220 mg, 1.2 mmol) in MeOH (20 mL) was cooled to −78° C. To this solution was bubbled ozone until the reaction turned blue. Nitrogen was bubbled through the reaction to drive off excess ozone, followed by addition of DMS (0.870 mL, 11.7 mmol). The reaction was allowed to warm up to RT. The solvents were removed under reduced pressure. The crude product was purified by flash chromatography to afford (4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde. 1H-NMR (500 MHz, CDCl3) δ ppm 9.78 (s, 1H), 7.75 (d, J=7.5 Hz, 1H), 7.34 (d, J=7.5 Hz, 1H), 5.27 (s, 2H), 3.90 (s, 2H), 2.23 (s, 3H).

Workup

  1. customTo this solution was bubbled ozone until the reaction
  2. customNitrogen was bubbled through the reaction
  3. customThe solvents were removed under reduced pressure
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5b3392d0b99e40fabcc63469cc2062dc
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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