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

HRID 613386Notes

Reaction equation

HRID 613386 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[CH:21]=[C: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[CH:21]=[C: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 54150655ethyl (+/-)-3-[4-(2-tetrahydropyranyloxy)-1-butyl]-5H-dibenzo[a,d]cycloheptene-10-acetate

Product 1

HCID 53688679Ethyl (+/-)-3-[4-hydroxy-1-butyl]-5H-dibenzo[a,d]cycloheptene-10-acetateYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl (±)-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) Rf 0.49; 1H NMR (250 MHz, CDCl3) δ 6.85-7.25 (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-56f5a07a786342889be79e6f7558dec9
Source dataset
uspto-grants-1999_12
Patent number
US06008213

Reaction notes

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