p-Toluenesulfonic acid monohydrate → Ethyl (+/-)-10,11-dihydro-3-(4-hydroxy-1-butyl)-5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 1369235Notes

Reaction equation

HRID 1369235 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12071463Ethyl (+/-)-10,11-dihydro-3-[4-(2-tetrahydropyranyloxy)-1-butyl)-5H-dibenzo[a,d]cycloheptene-10-acetate

Product 1

HCID 12071464Ethyl (+/-)-10,11-dihydro-3-(4-hydroxy-1-butyl)-5H-dibenzo[a,d]cycloheptene-10-acetateYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl (±)-10,11-dihydro-3-[4-(2-tetrahydropyranyloxy)-1-butyl]-5H-dibenzo[a,d]cycloheptene-10-acetate (456.0 mg, 1.04 mmole) and p-toluenesulfonic acid monohydrate (60 mg, 0.31 mmole) in absolute EtOH (10 mL) was stirred at RT. After 2 hr, the reaction was quenched with 5% NaHCO3 (1 mL) and concentrated to remove the EtOH. The residue was diluted with H2O (2 mL) and extracted with CH2Cl2. Drying (MgSO4), concentration, and silica gel chromatography (1:1 EtOAc/hexanes) gave the title compound (342.4 mg, 93%) as a colorless oil: TLC (1:1 EtOAc/hexanes) Rf0.49; 1H NMR (250 MHz, CDCl3) δ6.85-7.25 (m, 7 H), 4.34 (d, J=15.1 Hz, 1 H), 4.08-4.30 (m, 2 H), 3.75-3.95 (m, 2 H), 3.53-3.72 (m, 2 H), 3.33 (dd, J=15.1, 4.1 Hz, 1 H), 2.95 (dd, J=15.1, 9.4 Hz, 1 H), 2.40-2.75 (m, 4 H), 1.45-1.80 (m, 4 H), 1.27 (t, J=7.1 Hz, 3 H); MS (ES) m/e 353 (M+H)+.

Workup

  1. customthe reaction was quenched with 5% NaHCO3 (1 mL)
  2. concentrationconcentrated
  3. customto remove the EtOH
  4. additionThe residue was diluted with H2O (2 mL)
  5. extractionextracted with CH2Cl2
  6. customDrying
  7. concentration(MgSO4), concentration, and silica gel chromatography (1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-ec09fa0d6a734c94867dfd04d785b4ac
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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