Carbon Dioxide → HCID 23118632, compound

HRID 2378722Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH:8]([O:11][CH3:12])[O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C([Li])CCC.[C:27](=[O:29])=[O:28]>C1COCC1>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:6]1[CH:5]=[CH:4][C:3]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:2]([CH:7]=1)[C:27]([OH:29])=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-bromo-5-dimethoxymethyl-2-(2-morpholinoethoxy)benzene (3.11 g, 8.63 mmol) obtained in Step 3 in THF (40.0 mL) was cooled to −78° C., to which n-butyllithium (1.60 mol/L, 20.0 mL, 32.0 mmol) was added dropwise for 3 minutes, followed by stirring at −78° C. for 5 minutes. The reaction mixture was added with dry ice and was stirred for 3 hours while warming to room temperature. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was added with a 1 mol/L aqueous ammonium acetate solution (30 mL), was purified by HP-20 column chromatography (water, then acetonitrile/water=2/1), then crystallized from mixed solvent of ethyl acetate/hexane (1/1) to obtain 5-dimethoxymethyl-2-(2-morpholinoethoxy)benzoic acid (0.58 g, 21%).

Workup

additionwas added dropwise for 3 minutes
stirringwas stirred for 3 hours
temperaturewhile warming to room temperature
customThe solvent of the reaction mixture was evaporated under reduced pressure
additionThe residue was added with a 1 mol/L aqueous ammonium acetate solution (30 mL)
customwas purified by HP-20 column chromatography (water
customacetonitrile/water=2/1), then crystallized
additionfrom mixed solvent of ethyl acetate/hexane (1/1)

Sources & evidence

ORD record: ord-07ea007c12774acab4204bd3b6ed97b9
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470717B2

Reaction notes

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