Methanol → HCID 68752781, compound

HRID 1912933Notes

Reaction equation

HRID 1912933 reaction equation
[CH3:1][C:2]1([CH2:11][C:12]([O:14]CC)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.CO.[OH-].[Na+]>O1CCCC1.O>[CH3:1][C:2]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86665180(+/-)-ethyl 2-(1-methyl-2,3-dihydro-1H-inden-1-yl)acetate

Product 1

HCID 68752781HCID 68752781, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 131A (0.47 g, 2.1 mmol) in tetrahydrofuran (6 mL), water (3 mL), and methanol (6 mL) was added 5N NaOH aqueous solution (2.1 mL, 10.8 mmol). After stirring at room temperature for 4 hours, the reaction mixture was concentrated to half the volume, diluted with water (10 mL), washed with methylene chloride (10 mL), acidified to pH˜2 with aqueous 3N HCl solution, and extracted with methylene chloride (3×15 mL). The combined organic extracts were washed with H2O (50 mL), brine (50 mL), dried over MgSO4, filtered, and concentrates under reduced pressure to obtain 0.32 g of the title compound. MS (DCI/NH3) m/z 208 (M+NH4)+

Workup

  1. concentrationthe reaction mixture was concentrated to half the volume
  2. additiondiluted with water (10 mL)
  3. washwashed with methylene chloride (10 mL)
  4. extractionextracted with methylene chloride (3×15 mL)
  5. washThe combined organic extracts were washed with H2O (50 mL), brine (50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-37ea14ba114f434cbb11e34c6cfe14f8
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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