Dichloromethane → HCID 21839655, compound

HRID 1738889Notes

Reaction equation

HRID 1738889 reaction equation
S([O-])(=O)(=O)C.ClCCl.[CH3:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C([O:18][CH2:19][CH3:20])(=O)C>>[CH2:11]([C:10]1[CH2:13][CH:12]2[CH2:11][CH:10]([CH2:9][C:19](=[O:18])[CH2:20]2)[CH:9]=1)[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 85257MethanesulfonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 21839655HCID 21839655, compoundYield 41%

Procedure

This reaction was performed in a manner similar to that described for the preparation of IIc, starting from mesylate IV (X=--CH2 --; R=n--C4H9) (13.6 g, 47.2 mmol), silica gel (14 g) and dichloromethane (140 ml). The residue obtained was subjected to column chromatography on silica gel (120 g) using hexane/ethyl acetate mixtures of increasing polarity as eluent. On elution with 95:5 hexane/ethyl acetate, the ketone IIe (3.7 g, 41% yield) was obtained. Continuing the elution with 90:10 hexane/ethyl acetate, alcohol V (X=--CH2 --; R=n--C4H9) (2.8 g, 28% yield) was obtained.

Workup

  1. customthat described for the preparation of IIc
  2. customThe residue obtained
  3. temperatureof increasing polarity as eluent
  4. washOn elution with 95:5 hexane/ethyl acetate

Sources & evidence

ORD record
ord-317c25e685cc423dbc3585bbb16fdbf9
Source dataset
uspto-grants-1999_10
Patent number
US05965569

Reaction notes

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