HCID 15595179, compound → HCID 15595180, compound

HRID 1906211Notes

Reaction equation

HRID 1906211 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:30]=[CH:29][C:9]2[C:10](=[O:28])[CH2:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21]C3CCCCO3)([CH3:14])[O:13][C:8]=2[C:7]=1[CH2:31][CH2:32][CH3:33]>CO.Cl>[CH3:1][O:2][C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:30]=[CH:29][C:9]2[C:10](=[O:28])[CH2:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])([CH3:14])[O:13][C:8]=2[C:7]=1[CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 1

HCID 15595179HCID 15595179, compound

Product 1

HCID 15595180HCID 15595180, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2.3 g of the chromanone product from Example 2 in 25 ml of methanol and 5 ml of 2N hydrochloric acid was stirred for 1.75 hours at room temperature then concentrated in vacuo to remove most of the methanol. The residue was diluted with water, neutralized with sodium bicarbonate, and extracted 4 times with ether. The combined ether extracts were washed with water and brine, dried (magnesium sulfate), filtered, and concentrated in vacuo in yield 1.85 g of an oil. This material was purified by HPLC (silica gel, 1.5:1 ethyl acetate-hexane) giving 1.65 g (87.1%) of rac.-[[3,4-dihydro-2-(6-hydroxyhexyl)-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]acetic acid methyl ester as a yellow oil.

Workup

  1. concentrationthen concentrated in vacuo
  2. customto remove most of the methanol
  3. additionThe residue was diluted with water
  4. extractionextracted 4 times with ether
  5. washThe combined ether extracts were washed with water and brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo in yield 1.85 g of an oil
  9. customThis material was purified by HPLC (silica gel, 1.5:1 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-bc82c18d56c34781a14d65a12db2c3f7
Source dataset
uspto-grants-1987_03
Patent number
US04650812

Reaction notes

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