Phosphate → 2-Carboxymethylthio-2-methyltetrahydrofuran

HRID 55557Notes

Reaction equation

HRID 55557 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:18][C:19]1[O:20][CH2:21][CH2:22][CH:23]=1.P([O-])([O-])([O-])=O>ClCCl.O.C(OCC)(=O)C>[C:3]([CH2:2][S:1][C:19]1([CH3:18])[CH2:23][CH2:22][CH2:21][O:20]1)([OH:5])=[O:4]

Participants

8

Reactant 4

HCID 1061PhosphateHCID 1133Thioglycolic AcidHCID 151452,3-Dihydro-5-methylfuranHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 199579892-Carboxymethylthio-2-methyltetrahydrofuran

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of mercaptoacetic acid (10 mmol) in 5 mL of dichloromethane containing p-toluenesulfonic acid mono-hydrate (100 mg) is cooled with stirring to -10° to -25° C. 2-Methyl-4,5-dihydrofuran (10 mmol) in 10 mL of dichloromethane is added dropwise to the cold solution while the temperature is maintained between -10° C. to -25° C. Then 5 mL of phosphate buffer is added and the solution is allowed to come to room temperature. The mixture is poured into a 30 mL of ethyl acetate and 10 mL of water. Organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined ethyl acetate layer is dried and evaporated to give 26 as a colorless oil.

Workup

  1. temperatureis cooled
  2. temperatureis maintained between -10° C. to -25° C
  3. customto come to room temperature
  4. customOrganic layer is separated
  5. extractionthe aqueous layer is extracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate layer is dried
  7. customevaporated

Sources & evidence

ORD record
ord-8a84ce7bcd39449b8c918245109bf273
Source dataset
uspto-grants-1997_04
Patent number
US05625075

Reaction notes

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