Phosphorus pentachloride → HCID 71463896, compound

HRID 404536Notes

Reaction equation

HRID 404536 reaction equation
[CH3:1][C@H:2]1[C@H:34]([CH3:35])[C@@H:33]2[C@@:5]([CH3:37])([CH2:6][CH2:7][C@@:8]3([CH3:36])[C@:14]4([CH3:32])[CH2:15][CH2:16][C@H:17]5[C@:22]([C:24]([OH:26])=[O:25])([CH3:23])[C@H:21]([O:27][C:28]([CH3:30])=[O:29])[CH2:20][CH2:19][C@:18]5([CH3:31])[C@H:13]4[C:11](=[O:12])[CH:10]=[C:9]32)[CH2:4][CH2:3]1.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][C@H:2]1[C@H:34]([CH3:35])[C@@H:33]2[C@@:5]([CH3:37])([CH2:6][CH2:7][C@@:8]3([CH3:36])[C@:14]4([CH3:32])[CH2:15][CH2:16][CH:17]5[C@:22]([C:24]([OH:26])=[O:25])([CH3:23])[C@H:21]([O:27][C:28]([CH3:30])=[O:29])[CH2:20][CH2:19][C@:18]5([CH3:31])[C@H:13]4[C:11](=[O:12])[CH:10]=[C:9]32)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 11168203Acetyl-11-keto-beta-boswellic acid

Product 1

HCID 71463896HCID 71463896, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-O-acetyl-11-keto-β-boswellic acid (5 g, 0.0097 mol), 3 mL of chloroform taken in a round bottom flask. Then phosphorous pentachloride (16 g; 0.078 mol) was added to reaction mixture (RM) at Room temperature. RM was stirred at 50° C. for 1 hr, then stirred at RT for 4 hours. Then RM was poured in ice cold water, extracted with Ethyl acetate (EtOAc), organic layer was washed with brine, dried over sodium sulphate and concentrated. The crude was subjected to column chromatography, hexane/acetone as an eluent. Compound eluted in 15% acetone in hexane. [Yield 2 g; Percentage of yield is 39.2%].

Workup

  1. customtaken in a round bottom flask
  2. stirringstirred at RT for 4 hours
  3. additionThen RM was poured in ice cold water
  4. extractionextracted with Ethyl acetate (EtOAc), organic layer
  5. washwas washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. washCompound eluted in 15% acetone in hexane

Sources & evidence

ORD record
ord-0da3abff07724644a19d51e61b4b750f
Source dataset
uspto-grants-2014_06
Patent number
US08748598B2

Reaction notes

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