Water → HCID 68461644, compound

HRID 2358272Notes

Reaction equation

HRID 2358272 reaction equation
[I-].[K+].Cl[CH2:4][CH2:5][CH2:6][C:7]1([CH3:12])[O:11][CH2:10][CH2:9][O:8]1.[CH3:13][C:14]12[C:22](=[O:23])[CH2:21][CH2:20][CH:19]1[CH:18]([O:24][CH2:25][CH:26]=[O:27])[C:17](=[O:28])[CH2:16][CH2:15]2.O>CN(C=O)C.C1C=C2C3[N-]C(C2=CC=1)=NC1=NC(C2C1=CC=CC=2)=NC1=NC(C2C1=CC=CC=2)=NC1[N-]C(=C2C=1C=CC=C2)N=3.[Co+2].[Cr](Cl)(Cl)=O>[OH:27][CH:26]([CH2:4][CH2:5][CH2:6][C:7]1([CH3:12])[O:11][CH2:10][CH2:9][O:8]1)[CH2:25][O:24][CH:18]1[C:17](=[O:28])[CH2:16][CH2:15][C:14]2([CH3:13])[CH:19]1[CH2:20][CH2:21][C:22]2=[O:23]

Participants

8

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolaneHCID 73225619(7a-Methyl-1,5-dioxo-octahydro-inden-4-yloxy)-acetaldehyde

Product 1

HCID 68461644HCID 68461644, compound

Reagents, catalysts & solvents 3

HCID 178486305HCID 178486305, compoundCatalystHCID 178526110HCID 178526110, compoundCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Potassium iodide (31.1 g, 187.5 mmol, 3 eq) was added to a solution of 2-(3-chloro-propyl)-2-methyl-[1,3]dioxolane (18.8 mL, 125 mmol, 2 eq) in DMF (50 mL) and the reaction mixture was stirred at 60° C. in dark for 6 h. The reaction mixture was then cooled to room temperature and then combined with (7a-Methyl-1,5-dioxo-octahydro-inden-4-yloxy)-acetaldehyde (14 g, 62.5 mmol) in DMF (150 mL). To the stirred mixture at 0° C., was added cobalt phthalocyanine (357 mg, 0.625 mmol, 0.01 eq), followed by chromous chloride (23.1 g, 187.5 mmol, 3 eq) portion-wise, resulting in release of heat. The reaction mixture was allowed to stir from 0° C. slowly to room temperature for 24 h. The reaction mixture was then cooled to 0° C. and cold water (200 mL) was added. The resulting mixture was extracted with pentane (200 mL). The aqueous layer was extracted with dichloromethane (4×200 mL). The combined organic layer was dried with magnesium sulfate, filtered, the solvent was removed together with toluene (2×100 mL) under reduced pressure, and the resulting residue purified by flash chromatography 20-70% ethyl acetate in hexane to yield the tile compound as an oil, as 1:1 mixture of two diastereomers.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customresulting in release
  3. temperatureof heat
  4. stirringto stir from 0° C. slowly to room temperature for 24 h
  5. temperatureThe reaction mixture was then cooled to 0° C.
  6. extractionThe resulting mixture was extracted with pentane (200 mL)
  7. extractionThe aqueous layer was extracted with dichloromethane (4×200 mL)
  8. dry with materialThe combined organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed together with toluene (2×100 mL) under reduced pressure
  11. customthe resulting residue purified by flash chromatography 20-70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-00952e717aa44c2faa2f3f98516b3aa1
Source dataset
uspto-grants-2010_07
Patent number
US07763648B2

Reaction notes

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