Chloroform → HCID 68451881, compound

HRID 2353591Notes

Reaction equation

HRID 2353591 reaction equation
[CH3:1][C:2]1([CH3:13])[CH:7]2[CH:3]1[CH2:4][C:5](=[O:12])[CH:6]2[C:8](=O)[CH2:9][CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)[Cl:34]>C(Cl)(Cl)(Cl)Cl>[Cl:34][C:8](=[C:6]1[C:5](=[O:12])[CH2:4][C@H:3]2[C@@H:7]1[C:2]2([CH3:13])[CH3:1])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 11776Triphenylphosphine2×HCID 68453922HCID 68453922, compound

Product 1

HCID 68451881HCID 68451881, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of rac-(1S,5R)-6,6-dimethyl-2-propionyl-bicyclo[3.1.0]hexan-3-one (14.37 g, 80 mmol) in chloroform (145 mL) and CCl4 (53 mL), triphenylphosphine (41.8 g, 160 mmol) is added. The resulting solution is stirred at 60° C. for 75 min before a second portion of triphenylphosphine (4.2 g, 16 mmol) is added. Stirring is continued at 60° C. for 30 min. The solvent is evaporated and the residue is suspended in pentane. The pentane solution is decanted from the brown oily residue. The residue is once more treated with pentane. The combined pentane fractions are carefully evaporated to leave crude (1R,5S)-2-[1-chloro-propylidene]-6,6-dimethyl-bicyclo[3.1.0]hexan-3-one (11.0 g) as a yellow oil.

Workup

  1. additionis added
  2. customThe solvent is evaporated
  3. customThe pentane solution is decanted from the brown oily residue
  4. additionThe residue is once more treated with pentane
  5. customThe combined pentane fractions are carefully evaporated

Sources & evidence

ORD record
ord-86ef30a2fd5f447e9ff1dda46383b379
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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