Dichloromethane → HCID 13349252, compound

HRID 364334Notes

Reaction equation

HRID 364334 reaction equation
[Cl-].C([Al+][CH2:5][CH3:6])C.[CH2:7](Cl)Cl.CS(O[C@H]([C:17]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]C)([OH:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])C)(=O)=O>P(=O)(O)(O)O.C(OCC)(=O)C>[CH3:7][C@@H:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:5][CH3:6])[C:17](=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 13349246HCID 13349246, compoundHCID 16686102Diethyl aluminum chloride

Product 1

HCID 13349252HCID 13349252, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 1004Phosphoric AcidCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

After 0.63 ml (0.63 mmol) of diethylaluminum chloride (hexane 1M solution) were added to a dried methylene chloride (3 ml) solution of 89.7 mg (0.24 mmol) of (S)-2-methanesulfonyloxy-3-octyl-3-undecanol (unrefined) at -78° C. under stirring, and stirred for two and a half hours at -78° C., the temperature was raised to 0° C. over an hour and a half. The reaction was stopped with three drops of phosphoric acid buffer solution (pH 7). The resultant suspension was diluted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated. The oily residue was separated and refined by the use of silica gel column chromatography (hexane/ethyl acetate=35/1) to obtain (S)-10-methyl-9-octadecanone as a colorless oily substance (60.5 mg, yield 90%).

Workup

  1. stirringstirred for two and a half hours at -78° C.
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oily residue was separated

Sources & evidence

ORD record
ord-524551429d3e4fc2bae4047df7efb279
Source dataset
uspto-grants-1986_08
Patent number
US04604486

Reaction notes

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