Hydrochloric Acid → HCID 68726754, compound

HRID 1471401Notes

Reaction equation

HRID 1471401 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([O-])([O-])=O.[K+].[K+].[CH2:21](I)[CH3:22].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][CH2:21][CH3:22])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 68723612HCID 68723612, compound

Product 1

HCID 68726754HCID 68726754, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 5° C., a solution of the previously obtained 7-methylenespiro[4.5]decane-6-carboxylic acid (1.2 g, 6.2 mmol) in DMF (30 ml) was treated with K2CO3 (0.94 g, 6.8 mmol). The resulting mixture was stirred for 30 min., treated with ethyl iodide (0.75 ml, 9.3 mmol), stirred at 20° C. for 2 h, poured into cold 2N aqueous HCl (20 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 (90 g SiO2, hexane/MTBE 98:2) of the crude product (1.23 g) gave ethyl 7-methylenespiro[4.5]decane-6-carboxylate (0.69 g, 50%). Boiling point: 90° C. (0.08 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-078c1a56b9204d6b8fe0bf4b33b30850
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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