Methyl iodide → HCID 53807096, compound

HRID 1598433Notes

Reaction equation

HRID 1598433 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]2[C:16]=1[CH2:17][CH:18]([C:27]([O:29][CH3:30])=[O:28])[O:19][CH2:20]2.CI.[NH4+].[Cl-]>C1COCC1.O>[CH3:30][O:29][C:27]([C:18]1([CH3:1])[CH2:17][C:16]2[C:21](=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:15]=2[O:14][CH3:13])[CH2:20][O:19]1)=[O:28]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 15370482HCID 15370482, compoundHCID 178418339Butyllithium

Product 1

HCID 53807096HCID 53807096, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of di-isopropylamine (616.8 μl, 4.37 mmol) in THF (10 ml) was cooled to 0° C. and degassed briefly. n-Butyl lithium (1.6M in hexane, 2.60 ml, 4.17 mmol) was added. After stirred for 30 minutes at 0° C., the solution was further cooled to -78° C. A solution of 5,8-dimethoxy-3-methoxycarbonylisochroman (1.0 g, 3.97 mmol) in THF (10 ml), pre-degassed, was added slowly. The resulting yellow solution was stirred for 1 hour at -78° C. before the addition of methyliodide (1.01 ml, 16 mmol). After stirred further for 45 minutes, sat. NH4Cl solution was added. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried and evaporated to give a crude product which was chromatographed (hexane:EtOAc=3:1) to give the desired product as a solid (650 mg, m p. 73.0°-74.5° C.) and another fraction (192 mg) which contained 66% of titled product and 34% of the starting material.

Workup

  1. customdegassed briefly
  2. temperaturethe solution was further cooled to -78° C
  3. additionwas added slowly
  4. stirringAfter stirred further for 45 minutes
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. customevaporated
  8. customto give a crude product which
  9. customwas chromatographed (hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-54b45017ea55457b96f25cbeb5dc345a
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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