Water → HCID 19920480, compound

HRID 1461218Notes

Reaction equation

HRID 1461218 reaction equation
[C:1]([CH2:4][S:5][C:6]1([CH3:11])[CH2:10][CH2:9][CH2:8][O:7]1)(O)=[O:2].O>O1CCCC1>[OH:2][CH2:1][CH2:4][S:5][C:6]1([CH3:11])[CH2:10][CH2:9][CH2:8][O:7]1

Participants

4

Reactant 2

HCID 962WaterHCID 199579892-Carboxymethylthio-2-methyltetrahydrofuran

Product 1

HCID 19920480HCID 19920480, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2 mmol of 26 in 10 mL of anhydrous tetrahydrofuran (kept at 0° C.) 3 mL of BH3. THF complex (1M) is added slowly. The mixture is stirred for 3 hours in a nitrogen atmosphere at 0° C. Approximately 10 mL of water added slowly and the reaction is stirred for 15 min. The mixture is concentrated in vacuo at 40°-45° C. and the aqueous residue is extracted with ethyl acetate. The organic layer is washed with 10% bicarbonate. The ethyl acetate layer is dried and evaporated to give the product, 27 as an oil.

Workup

  1. additionTHF complex (1M) is added slowly
  2. stirringthe reaction is stirred for 15 min
  3. concentrationThe mixture is concentrated in vacuo at 40°-45° C.
  4. extractionthe aqueous residue is extracted with ethyl acetate
  5. washThe organic layer is washed with 10% bicarbonate
  6. dry with materialThe ethyl acetate layer is dried
  7. customevaporated

Sources & evidence

ORD record
ord-ad9afeedc27b4a33b829de1fdb9d7135
Source dataset
uspto-grants-1991_12
Patent number
US05075099

Reaction notes

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