Chloroform → HCID 46193619, compound

HRID 919187Notes

Reaction equation

HRID 919187 reaction equation
[OH:1][C:2]1[C:10]2[C:9]3[C:11]([OH:16])=[CH:12][C:13]([OH:15])=[CH:14][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].C(Cl)(Cl)Cl.[C:26](Cl)(=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29]>C(=S)=S>[OH:1][C:2]1[C:10]2[C:9]3[C:11]([OH:16])=[CH:12][C:13]([OH:15])=[C:14]([C:26](=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29])[C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([OH:17])[C:3]=1[C:2](=[O:1])[CH2:10][CH:9]([CH3:11])[CH3:8]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 66054Isovaleryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10775914HCID 10775914, compound

Product 1

HCID 46193619HCID 46193619, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
50 °C

Procedure

Compound 8 (100 mg, 0.431 mmol) and aluminum trichloride (287 mg, 2.15 mmol) were suspended in 5 mL of carbon disulfide at rt. Chloroform (6 mL) was added to the suspension and the reaction mixture was warmed to 50° C. in a water-bath. Isovaleryl chloride (259 mg, 2.15 mmol) was added dropwise and the reaction was stirred for 2 h at 50° C. After removing solvent in vacuo, and the crude reaction mixture was purified by column chromatography (1-5% ethyl acetate/hexane) to yield 3 (30 mg, 17%) as a white solid.

Workup

  1. customAfter removing solvent in vacuo
  2. customthe crude reaction mixture
  3. customwas purified by column chromatography (1-5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-85d4ba21242b4db390aba66d541f5bc6
Source dataset
uspto-grants-2016_03
Patent number
US09273021B2

Reaction notes

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