Benzoyl chloride → HCID 18534541, compound

HRID 411962Notes

Reaction equation

HRID 411962 reaction equation
[C:1]1(O)([C:9]2([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:5][CH2:4][CH:3](O)[C:2]1([OH:8])[OH:7].C1COCC1.C(Cl)(=O)C1C=CC=CC=1.CCN(CC)CC>C(OCC)(=O)C.O>[C:2]([OH:7])(=[O:8])[C:3]1[CH:4]=[CH:5][CH:1]=[CH:9][CH:14]=1.[C:2]([OH:7])(=[O:8])[C:3]1[CH:4]=[CH:5][CH:1]=[CH:9][CH:14]=1.[C:2]([OH:7])(=[O:8])[C:3]1[CH:4]=[CH:5][CH:1]=[CH:9][CH:14]=1.[C:2]([OH:7])(=[O:8])[C:3]1[CH:4]=[CH:5][CH:1]=[CH:9][CH:14]=1.[C:2]([OH:7])(=[O:8])[C:3]1[CH:4]=[CH:5][CH:1]=[CH:9][CH:14]=1.[C:2]([OH:7])(=[O:8])[C:3]1[CH:4]=[CH:5][CH:1]=[CH:9][CH:14]=1.[CH:14]1([C:9]2([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86758963HCID 86758963, compound

Product 1

HCID 18534541HCID 18534541, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The ter-cyclopentane tetra-ol (0.75 g, 1.25 mmol) was dissolved into 0.1 M THF at room temperature. Added benzoyl chloride (0.88 ml, 7.55 mmol) to the tetra-ol solution, and stirred at room temperature for 5 min, before adding Et3N (1.08 ml, 7.75 mmol). After stirring at room temperature for 10 min, reaction became slightly cloudy. After stirring for 24 hr at room temperature, reaction was diluted with ethyl acetate and poured into water (20 ml). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3×20 ml). The organic extracts were pooled, and washed sequentially with 10% aq HCl solution (10 ml), water (10 ml), and sat aq Na2CO3 (10 ml). The layers were separated and the organic layer was dried over Na2SO4, filtered, and reduced in vacuo to afford a golden yellow residue. Purification of the residue via flash chromatography (silica, 75:25 hexanes:ethyl acetate) afforded the ter-cyclopentane hexa-benzoate (0.76 mg, 60% yield) as an off-white solid.

Workup

  1. customreaction
  2. stirringAfter stirring for 24 hr at room temperature
  3. customreaction
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×20 ml)
  6. washwashed sequentially with 10% aq HCl solution (10 ml), water (10 ml)
  7. customThe layers were separated
  8. dry with materialthe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. customto afford a golden yellow residue
  11. customPurification of the residue via flash chromatography (silica, 75:25 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-3f138370e35d44b8830177b3fd4eda16
Source dataset
uspto-grants-2003_05
Patent number
US06562782B1

Reaction notes

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