Potassium Hydroxide → HCID 69206624, compound

HRID 2374120Notes

Reaction equation

HRID 2374120 reaction equation
C1(C)C=CC(S(OCCCCCC[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)(=O)=O)=CC=1.[OH-:31].[K+].[CH:33]1([CH2:37][OH:38])[CH2:36][CH2:35][CH2:34]1>CS(C)=O>[Br:29][C:26]1[CH:25]=[CH:24][C:23]([C:20]2[CH:19]=[CH:18][C:17]([O:31][CH2:21][CH2:22][CH2:17][CH2:18][CH2:19][CH2:20][O:38][CH2:37][CH:33]3[CH2:36][CH2:35][CH2:34]3)=[CH:22][CH:21]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 78130CyclobutylcarbinolHCID 86760779HCID 86760779, compound

Product 1

HCID 69206624HCID 69206624, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of (4′-Bromobiphenyl-4-yl)hexyl toluene-p-sulphonate (2.50 g, 5.0 mmol) from step 2 in DMSO (50 ml) was cooled to −5° C. and potassium hydroxide powder (Fluka, 1.03 g, 0.018 mol) was added and the mixture was stirred using a mechanical stirrer, a solution of cyclobutylmethanol (0.80 g, 10.0 mmol) in DMSO (15 ml) was added dropwise. The reaction mixture was kept at −5° C. for 1 h and then removed from the cooling bath for a further 2 h. The product was extracted in hexane (150 ml) and washed with water in order to remove all traces of DMSO. Hexane was removed under reduced pressure and the residue was purified by column chromatography [DCM-hexane, 1:6] to give a white powder.

Workup

  1. customremoved from the cooling bath for a further 2 h
  2. extractionThe product was extracted in hexane (150 ml)
  3. washwashed with water in order
  4. customto remove all traces of DMSO
  5. customHexane was removed under reduced pressure
  6. customthe residue was purified by column chromatography [DCM-hexane, 1:6]
  7. customto give a white powder

Sources & evidence

ORD record
ord-5ac606ac66f34d9abf2ef5bfdf7bc5f0
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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