Water → HCID 19895299, compound

HRID 892408Notes

Reaction equation

HRID 892408 reaction equation
[OH:1][CH:2]=[C:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1.[CH3:15]I.O>C1COCC1>[CH3:15][O:1][CH:2]=[C:3]1[CH2:4][O:5][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 19895297HCID 19895297, compound

Product 1

HCID 19895299HCID 19895299, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of HNa (50%, 1.06 gr) in 40 ml of dry THF, stirred at 0° C., a solution of 5.12 gr of 4 in 40 ml THF was added dropwise. After 30 min, CH3I (6.6 ml) was added and the mixture was stirred at 0° C. for 6 hours, then overnight at room temperature. Water was added and the mixture was extracted with diethyl-ether, the organic layer was washed with water until neutral, then with brine, dried and evaporated. The residue was purified on alumina column (eluent CH2Cl2) to yield 4.8 gr of 5 (86%).

Workup

  1. stirringthe mixture was stirred at 0° C. for 6 hours
  2. customovernight
  3. customat room temperature
  4. extractionthe mixture was extracted with diethyl-ether
  5. washthe organic layer was washed with water until neutral, then with brine
  6. customdried
  7. customevaporated
  8. customThe residue was purified on alumina column (eluent CH2Cl2)

Sources & evidence

ORD record
ord-7f8fc359d3764ec8a48a6591e021af12
Source dataset
uspto-grants-1992_06
Patent number
US05118674

Reaction notes

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