Hydrochloric Acid → HCID 86635827, compound

HRID 2383977Notes

Reaction equation

HRID 2383977 reaction equation
C[O:2][C:3]([C:5]1([Cl:30])[C:7]2([CH2:12][CH2:11][C:10]([C:28]#[N:29])([C:13]3[C:21]4[C:20]5[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=5[O:18][C:17]=4[C:16]([O:26][CH3:27])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[O:6]1)=[O:4].C[O-].[Na+].Cl>C(O)C.O>[Cl:30][C:5]1([C:3]([OH:4])=[O:2])[C:7]2([CH2:8][CH2:9][C:10]([C:28]#[N:29])([C:13]3[C:21]4[C:20]5[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=5[O:18][C:17]=4[C:16]([O:26][CH3:27])=[CH:15][CH:14]=3)[CH2:11][CH2:12]2)[O:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86635828HCID 86635828, compound

Product 1

HCID 86635827HCID 86635827, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

At room temperature and under nitrogen, to a solution of 2-chloro-6-cyano-6-(4-methoxy-dibenzofuran-1-yl)-1-oxa-spiro[2.5]octane-2-carboxylic acid methyl ester (0.300 g, 0.0007 mol) (as obtained in step 1) in a mixture of ethanol (5 ml) and water (0.15 ml) was added sodium methoxide (0.190 g, 0.0035 mol). The reaction mass was refluxed for 1 hr, and once the product has formed, the reaction mass was brought to room temperature and the pH was adjusted to 2 with dil. HCl and extracted with Ethyl acetate. The organic layer was dried with sodium sulfate and concentrated under vacuum to get the 2-chloro-6-cyano-6-(4-methoxy-dibenzofuran-1-yl)-1-oxa-spiro[2.5]octane-2-carboxylic acid. Yield 0.180 g (64%)

Workup

  1. temperatureThe reaction mass was refluxed for 1 hr
  2. customonce the product has formed
  3. customwas brought to room temperature
  4. extractionextracted with Ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-97ebce10daa1447bb88bf1cec2c63fd8
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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