Hydrochloric Acid → HCID 68725529, compound

HRID 1471402Notes

Reaction equation

HRID 1471402 reaction equation
[CH2:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:3]1[C:12]([OH:14])=[O:13].[C:15]([O-])([O-])=O.[K+].[K+].CI.Cl>CN(C=O)C>[CH2:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:3]1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68723612HCID 68723612, compound

Product 1

HCID 68725529HCID 68725529, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 5° C., a solution of the previously obtained 7-methylenespiro[4.5]decane-6-carboxylic acid (1.1 g, 5.66 mmol, prepared as described in Example 28) in DMF (20 ml) was treated with K2CO3 (0.86 g, 6.8 mmol). The resulting mixture was stirred for 30 min., treated with methyl iodide (0.53 ml, 8.5 mmol), stirred at 20° C. for 2 h, poured into cold 2N aqueous HCl (30 ml), and extracted twice with hexane (50 ml). The combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4), and concentrated. FC (30 g SiO2, hexane/MTBE 50:1) of the crude product (1 g) gave methyl 7-methylenespiro[4.5]decane-6-carboxylate (0.84 g, 71%). Boiling point: 90° C. (1.1 mbar).

Workup

  1. stirringstirred at 20° C. for 2 h
  2. extractionextracted twice with hexane (50 ml)
  3. washThe combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8075a1624af6419a939a5c75811ccb99
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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