Aluminum(III) Chloride → ethyl (+/-)-10,11-dihydro-3-hydroxy-5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 1108884Notes

Reaction equation

HRID 1108884 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C[O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=3[CH2:12][C:11]=2[CH:27]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=3[CH2:12][C:11]=2[CH:27]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 15462070Ethyl (+/-)-10,11 dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate

Product 1

HCID 15888083ethyl (+/-)-10,11-dihydro-3-hydroxy-5H-dibenzo[a,d]cycloheptene-10-acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous AlCl3 (1.38 g, 10.35 mmol) was added all at once to a solution of ethyl (±)-10,11-dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate (643.6 mg, 2.07 mmol) in anhydrous CH2Cl2 (21 mL) at 0° C. under argon. The yellow solution was warmed to RT and stirred for 3 h, then was cooled to 0° C. and quenched with cold 3 N HCl (10 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated. Silica gel chromatography (25% EtOAc/hexanes) gave the title compound as a nearly colorless oil (611.7 mg, 100%): TLC Rf 0.26 (20% EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) δ 7.03-7.22 (m, 4H), 6.93 (d, J=8.1 Hz, 1H), 6.69 (d, J=2.6 Hz, 1H), 6.58 (dd, J=8.1, 2.6 Hz, 1H), 5.00 (s, 1H), 4.25 (d, J=14.9 Hz, IH), 4.11-4.25 (m, 2H), 3.73-3.88 (m, 1H), 3.79 (d, J=14.9 Hz, 1H), 3.28 (dd, J=15.0, 4.1 Hz, 1H), 2.91 (dd, J=15.0, 9.3 Hz, 1H), 2.65 (dd, J=15.6, 4.9 Hz, 1H), 2.53 (dd, J=15.6, 9.5 Hz, 1H), 1.27 (t, J=7.2 Hz, 3H), FTIR (CCl4) 3611 (sharp), 3447 (broad), 1734, 1504, 1291, 1272, 1176, 1152 cm-1 ; MS (ES) m/e 314.2 (M+NH4)+, 297.2 (M+H)+.

Workup

  1. temperaturewas cooled to 0° C.
  2. customquenched with cold 3 N HCl (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9ff6c364641d4b24b44f2c46ab430d0c
Source dataset
uspto-grants-2000_05
Patent number
US06069158

Reaction notes

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