HCID 10308881, compound → HCID 88629234, compound

HRID 236416Notes

Reaction equation

HRID 236416 reaction equation
[CH2:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:14](=[O:21])[CH:15]=[C:16]([CH2:19][OH:20])[O:17][CH:18]=1)[CH2:2][CH3:3].CC(C)=[O:28].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH2:6].[O:21]=[C:14]1[C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:5]2[CH:22]=[CH:23][CH:24]=[CH:25][C:4]=2[CH2:1][CH2:2][CH3:3])=[CH:18][O:17][C:16]([C:19]([OH:28])=[O:20])=[CH:15]1

Participants

4

Reactant 2

HCID 10308881HCID 10308881, compoundHCID 131709961Jones' reagent2×

Product 1

HCID 88629234HCID 88629234, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution 3.53 g (10.2 mmole) of the title alcohol of Example 4 in 100 ml of acetone was added dropwise 22.7 ml (ca. 20.4 mmole) of 0.9M Jones reagent. The solution was warmed to 50° and an additional 11.4 ml (10.2 mmoles) of Jones reagent was added. After five hours at room temperature the reaction was quenched with 40 ml of isopropyl alcohol. The insolubles were removed by decanting and the supernatant was concentrated in vacuo. The residue was triturated with ethyl acetate and filtered, and the filtrate was reconcentrated. Recrystallization from ethyl acetate-hexane (2:1 by volume) afforded 1.8 g of the title compound as the monohydrate.

Workup

  1. temperatureThe solution was warmed to 50°
  2. customAfter five hours at room temperature the reaction was quenched with 40 ml of isopropyl alcohol
  3. customThe insolubles were removed
  4. customby decanting
  5. concentrationthe supernatant was concentrated in vacuo
  6. customThe residue was triturated with ethyl acetate
  7. filtrationfiltered
  8. customRecrystallization from ethyl acetate-hexane (2:1 by volume)

Sources & evidence

ORD record
ord-69d5d3afb1b04db2b98e2901072dc0d7
Source dataset
uspto-grants-1987_02
Patent number
US04644071

Reaction notes

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