Water → HCID 12774760, compound

HRID 1757960Notes

Reaction equation

HRID 1757960 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:13][CH:12]([OH:14])[CH:11]([CH2:15][C:16]([NH2:18])=[O:17])[CH:10]1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.O.C(O)(C)C>CC(C)=O.C(N(CC)CC)C>[O:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:21]1[O:20][CH2:19][CH:10]1[CH:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][C:12](=[O:14])[CH:11]1[CH2:15][C:16]([NH2:18])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 12774759HCID 12774759, compound

Product 1

HCID 12774760HCID 12774760, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-20 °C

Procedure

70 ml of Jones solution containing 19.32 g (0.193 mole) of CrO3 are added dropwise at -20° to -25° C. to a solution of 49.3 g (0.136 mole) of the alcohol of Example 2 in 350 ml of acetone. (Jones solution comprises 26.7 g of CrO3, 23 ml of concentrated H2SO4, and 21 ml of H2O made up to 100 ml.) The solution is stirred for a further 2 hours at -20° C., and an excess of i-propanol is then added at this temperature. The solution is neutralized with triethylamine, allowed to warm up to room temperature and filtered over Celite. The residue is washed thoroughly with acetone, the filtrate is concentrated almost to dryness and ethyl acetate is added to the residue. The organic phase is washed several times with half-saturated NaCl solution, and the combined aqueous phases are saturated with NaCl and extracted several times with ethyl acetate. The combined extracts are dried over MgSO4, concentrated and filtered over a short column (5 times the quantity of silica gel, developing solvent: ethyl acetate).

Workup

  1. temperatureto warm up to room temperature
  2. filtrationfiltered over Celite
  3. washThe residue is washed thoroughly with acetone
  4. concentrationthe filtrate is concentrated almost to dryness and ethyl acetate
  5. additionis added to the residue
  6. washThe organic phase is washed several times with half-saturated NaCl solution
  7. extractionextracted several times with ethyl acetate
  8. dry with materialThe combined extracts are dried over MgSO4
  9. concentrationconcentrated
  10. filtrationfiltered over a short column (5 times the quantity of silica gel

Sources & evidence

ORD record
ord-2a6ec628fbd542ab8d6c93622c7f25b4
Source dataset
uspto-grants-1983_02
Patent number
US04371542

Reaction notes

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