Bromotriphenylmethane → HCID 23329933, compound

HRID 225366Notes

Reaction equation

HRID 225366 reaction equation
[CH:1]1([CH2:6][CH:7]([OH:11])/[CH:8]=[CH:9]/[I:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:12]1([C:18](Br)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH:1]1([CH2:6][CH:7]([O:11][C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)/[CH:8]=[CH:9]/[I:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11692BromotriphenylmethaneHCID 13723992HCID 13723992, compound

Product 1

HCID 23329933HCID 23329933, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 21.4 g. of 4-cyclopentyl-1-iodo-1-trans-buten-3-ol (Example 179) in 170 ml. of dry pyridine containing 31 g. of triphenylmethyl bromide is heated on the steam-bath for 2 hours. The dark mixture is poured into 850 ml. of iced water and the resulting solution is extracted three times with ether. The combined extracts are washed with ice cold 2% hydrochloric acid until the washings are acidic, saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness. Trituration of the residue followed by filtration removes triphenylcarbinol. The mother liquor is taken to dryness and the residual syrup is chromatographed on 400 g. of florisil using hexane gives 32 g. (78%) of syrup which solidifies on standing. Recrystallization from hexane affords white crystals, m.p. 87°-88° C.

Workup

  1. additionA mixture of 21.4 g
  2. additionThe dark mixture is poured into 850 ml
  3. extractionof iced water and the resulting solution is extracted three times with ether
  4. washThe combined extracts are washed with ice cold 2% hydrochloric acid until the washings
  5. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  6. filtrationTrituration of the residue followed by filtration
  7. customremoves triphenylcarbinol
  8. customthe residual syrup is chromatographed on 400 g
  9. customgives 32 g
  10. customRecrystallization from hexane
  11. customaffords white crystals, m.p. 87°-88° C.

Sources & evidence

ORD record
ord-eb18c39fd31742a79fed10ed63cbc656
Source dataset
uspto-grants-1980_11
Patent number
US04236027

Reaction notes

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