Water → HCID 20253406, compound

HRID 638133Notes

Reaction equation

HRID 638133 reaction equation
OS(O)(=O)=O.[CH2:6]([OH:19])[CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH:16]([OH:18])[CH3:17].[OH2:20]>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[O:18]=[C:16]([CH3:17])[CH2:15][CH2:14][CH2:13][C:12]#[C:11][CH2:10][C:9]#[C:8][CH2:7][C:6]([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 20253402HCID 20253402, compound

Product 1

HCID 20253406HCID 20253406, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

Chromium trioxide (12.0 g, 120 mmol) was dissolved in 120 mL of 3.5M H2SO4 (420 mmol) and cooled to -5°. A solution of diol 11 (4.30 g, 22.2 mmol) in acetone (250 mL) was added dropwise over 4 hr. When the addition was complete, the mixture was warmed to 20° over 45 min, then poured into water (400 mL), and extracted with ether (4×150 mL). The combined ether extracts were washed with brine (3×50 mL), dried (MgSO4), and concentrated in vacuo. The crude product was flash chromatographed9 (hexane:EtOAc:AcOH, 75:75:1), yielding 1.83 g (40% yield) of a highly unstable yellow oil.

Workup

  1. temperaturecooled to -5°
  2. additionWhen the addition
  3. temperaturethe mixture was warmed to 20° over 45 min
  4. extractionextracted with ether (4×150 mL)
  5. washThe combined ether extracts were washed with brine (3×50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customyielding 1.83 g (40% yield) of a highly unstable yellow oil

Sources & evidence

ORD record
ord-dbcef8c5ffc84ad885cc7782040e3c2f
Source dataset
uspto-grants-1985_12
Patent number
US04560551

Reaction notes

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