Methanol → HCID 86752491, compound

HRID 1600380Notes

Reaction equation

HRID 1600380 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][O:10][C@H:11]1[CH2:15][C@H:14](O)[CH:13]=[CH:12]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(N(CC)CC)C.CS([Cl:28])(=O)=O.CO>C(Cl)Cl>[CH2:1]([O:3][P:4]([CH2:9][O:10][C@H:11]1[CH2:15][C@@H:14]([Cl:28])[CH:13]=[CH:12]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86752492HCID 86752492, compound

Product 1

HCID 86752491HCID 86752491, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Trans-1-diethylphosphonomethoxycyclopent-2-en-4-ol (220 mg, 0.88 mmol) was dissolved in CH2Cl2 (2 mL) and cooled to 0° C. under nitrogen. Triethylamine (192 mg, 192 mmol) was added followed by methanesulphonyl chloride (220 mg, 192 mmol) and the reaction mixture leftto stir for 0.5 hrs at 0° C. The reaction mixture was allowed to warm to room temperature and MeOH was added. The aqueous solution was diluted with CH2Cl2 (10 mL) and washed with water, saturated NaHCO3 and brine. The solution was dried (MgSO4), filtered, concentrated and then purified by flash column chromatography with 5% MeOH/95% CH2Cl2 (144 mg, 62%).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water, saturated NaHCO3 and brine
  3. dry with materialThe solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography with 5% MeOH/95% CH2Cl2 (144 mg, 62%)

Sources & evidence

ORD record
ord-e1c8674ba96e405aad290cc7d7cbc1b5
Source dataset
uspto-grants-1998_04
Patent number
US05744600

Reaction notes

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