Iodoethane → HCID 18770930, compound

HRID 479454Notes

Reaction equation

HRID 479454 reaction equation
Cl.[C:2]([CH2:5][N:6]1[CH2:11][CH2:10][C:9]2([CH:16]=[C:15]([C:17]3[CH:22]=[C:21](F)[C:20]([O:24]CC)=[C:19](F)[CH:18]=3)[C:14]3[CH:28]=[CH:29][CH:30]=[CH:31][C:13]=3[O:12]2)[CH2:8][CH2:7]1)([OH:4])=[O:3].C(=O)([O-])O.[Na+].[CH2:37](I)[CH3:38]>CN(C)C=O.C(OCC)(=O)C>[OH:24][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[C:14]3[CH:28]=[CH:29][CH:30]=[CH:31][C:13]=3[O:12][C:9]3([CH2:8][CH2:7][N:6]([CH2:5][C:2]([O:4][CH2:37][CH3:38])=[O:3])[CH2:11][CH2:10]3)[CH:16]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 18770973HCID 18770973, compound

Product 1

HCID 18770930HCID 18770930, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1′-Carboxymethyl-4-(4-hydroxyphenyl)spiro[2H-1-benzopyran-2,4′-piperidine]-1′-acetate (432 mg, 1 mmol., prepared according to Example 42), sodium hydrogen carbonate (176 mg, 2.1 mmol) in dry N,N-dimethylformamide (25 cm3) was added ethyl iodide (0.088 cm3, 1.1 mmol) and the mixture was heated to 80° C. for 2 h. Upon cooling, it was diluted with ethyl acetate (100 cm3) and washed with water (5×100 cm3). The organic solution was then dried over sodium sulfate before the solvent was removed in vacuo. The crude material was then passed through a short pad of silica first with dichloromethane (which was discarded) and then with ethyl acetate. The solvent was removed to afford the desired product (194 mg, 51%).

Workup

  1. temperatureUpon cooling
  2. washwashed with water (5×100 cm3)
  3. dry with materialThe organic solution was then dried over sodium sulfate before the solvent
  4. customwas removed in vacuo
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-3d610c2414da4bab9b6eebb19b803636
Source dataset
uspto-grants-2003_11
Patent number
US06645973B1

Reaction notes

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