4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester

HRID 418947Notes

Reaction equation

HRID 418947 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][OH:18])[CH:12]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].CCN(CC)CC.CNC1C=CC=C(NC)N=1>C(OCC)(=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][O:18][S:27]([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:12]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 111943672-N,6-N-dimethylpyridine-2,6-diamineHCID 66651951[6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanol

Product 1

HCID 72309434Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine [6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanol (1.45 g, 3.81 mmol), TosCl (0.80 g, 4.19 mmol), Et3N (1.2 mL, 8.38 mmol), 2,6-dimethylaminopyridine (140.0 mg, 1.14 mmol), and methylene chloride (30 mL), and stir under nitrogen atmosphere at room temperature. After 18 hours, concentrate reaction under vacuum and add ethyl acetate. Wash with water and then brine. Dry the organic phase with anhydrous sodium sulfate and concentrate to yield the titled compound (1.83 g, 95%) as a yellowish-white solid. TLC Rf=0.30 in 2:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.53 (d, 2H, J=8.4 Hz), 7.22 (d, 2H, J=8.4 Hz), 7.16 (d, 1H, J=8.8 Hz), 7.06 (d, 2H, J=8.8 Hz), 6.92 (d, 1H, J=2.2 Hz), 6.83 (d, 2H, J=8.4 Hz), 6.66 (dd, 1H, J=8.8, 2.6 Hz), 4.34 (dd, 1H, J=9.7, 2.6 Hz), 4.03 (dd, 1H, J=9.7, 4.0 Hz), 3.85 (s, 6H), 3.48 (d, 1H, J=11.9 Hz), 3.20 (s, 1H), 3.09 (dd, 1H, J=12.1, 3.3 Hz), 2.46 (s, 3H), 1.89 (m, 1H), 1.61 (m, 3H), 1.41 (d, 2H, J=9.7 Hz), 1.14 (m, 3H).

Workup

  1. concentrationconcentrate
  2. customreaction under vacuum
  3. washWash with water
  4. dry with materialDry the organic phase with anhydrous sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-5a96eff0621042b89c1a7eebc570c59c
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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