Styrene → HCID 70152332, compound

HRID 1018917Notes

Reaction equation

HRID 1018917 reaction equation
C=CC1C=CC=CC=1.C(C1C=CC=CC=1C=C)=C.[C:19]1([C:25]2[NH:26][C:27]3[C:32]([C:33]=2[CH2:34][CH2:35]OC2CCCCO2)=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC1C=CC(S([O-])(=O)=[O:51])=CC=1.C1C=C[NH+]=CC=1>ClCCCl.C(O)C>[C:19]1([C:25]2[NH:26][C:27]3[C:32]([C:33]=2[CH:34]([OH:51])[CH3:35])=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7501StyreneHCID 666661,2-DiethenylbenzeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 14969489HCID 14969489, compound

Product 1

HCID 70152332HCID 70152332, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1-[4-Benzyloxycarbamoyl]phenoxymethyl-copoly(styrene- 1%-divinylbenzene)-2-phenyl-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-indole (7.87 g) was suspended in a mixture of DCE (125 ml) and ethanol (12.5 ml) containing PPTS (5.83 g) and warmed to 70° C. for 18 h. The resin was then filtered off and washed with DMF (4×25 ml), DCM (4×25 ml), MeOH (4×25 ml) and ether (25 ml). A portion of the recovered resin (100 mg) was then suspended in dry DMF (3.0 ml) containing 5% pyrrolidine and heated to 110° C. for 4 h. The resin was filtered off and the solvent removed from the filtrate under reduced pressure to afford 2-phenyl-1H-indol-3-ylethanol. 1H (360 MHz, CDCl3) δ3.21 (2H, t, J=7.0 Hz), 3.97 (2H, t, J=7.0 Hz), 7.13-7.22 (2H, m), 7.38 (2H, m), 7.45 (2H, m), 7.62 (3H, m) and 8.12 (1H, br s).

Workup

  1. filtrationThe resin was then filtered off
  2. washwashed with DMF (4×25 ml), DCM (4×25 ml), MeOH (4×25 ml) and ether (25 ml)
  3. additioncontaining 5% pyrrolidine
  4. temperatureheated to 110° C. for 4 h
  5. filtrationThe resin was filtered off
  6. customthe solvent removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-d95dd0d9f08846508df441301de4bf40
Source dataset
uspto-grants-2002_11
Patent number
US06486153B1

Reaction notes

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