Sodium Hydroxide → HCID 118161815, compound

HRID 2203679Notes

Reaction equation

HRID 2203679 reaction equation
[O:1]1[CH2:4][C:3]2([CH2:9][CH:8]3[CH:6]([CH:7]3[C:10]([O:12]CC)=[O:11])[CH2:5]2)[CH2:2]1.[OH-].[Na+]>C(O)C.O>[O:1]1[CH2:4][C:3]2([CH2:5][CH:6]3[CH:8]([CH:7]3[C:10]([OH:12])=[O:11])[CH2:9]2)[CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118161660HCID 118161660, compound

Product 1

HCID 118161815HCID 118161815, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl spiro[bicyclo[3.1.0]hexane-3,3′-oxetane]-6-carboxylate (1.5 g, 7.6 mmol) in ethanol (15 mL) was added sodium hydroxide (917 mg, 22.9 mmol) in water (5 mL). After 16 h, the reaction mixture was concentrated, and the resulting residue was dissolved with water (20 mL). The resulting solution was extracted with ethyl acetate (15 mL). The aqueous layer was acidified with 1 M aqueous HCl solution to pH=3, and the aqueous solution was extracted with dichloromethane (20 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated to provide a white solid (0.80 g, 62% yield).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionthe resulting residue was dissolved with water (20 mL)
  3. extractionThe resulting solution was extracted with ethyl acetate (15 mL)
  4. extractionthe aqueous solution was extracted with dichloromethane (20 mL)
  5. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a8e918e24c604f168555b137a1b2b106
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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