Triethylamine → HCID 53655042, compound

HRID 356469Notes

Reaction equation

HRID 356469 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:20])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[S:28](Cl)([CH3:31])(=[O:30])=[O:29]>C(Cl)Cl>[C:14]1([CH2:13][CH2:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][O:1][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:6][CH:7]=2)=[O:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 187986891-[4-(2-Hydroxy-ethoxy)-phenyl]-3-phenyl-propan-1-one

Product 1

HCID 53655042HCID 53655042, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-[4-(2-hydroxy-ethoxy)-phenyl]-3-phenyl-propan-1-one (prepared in Example N; 6.0 g, 22.2 mmol) and triethylamine (NEt3) (4.60 mL, 33.3 mmol) in CH2Cl2 (50 mL) was cooled to 0° C. under a nitrogen atmosphere and treated with mesyl chloride (2.1 mL, 26.6 mmol). The mixture allowed to stir for 45 minutes, and then diluted with additional CH2Cl2 and washed with H2O. The organic layer was dried (MgSO4) and the solvent removed in vacuo to provide the title compound which was used without further purification. 1H NMR (DMSO-d6) δ 2.90 (t, 2 H), 3.20 (s, 3 H), 3.29 (t, 2 H), 4.32-4.34 (m, 2 H), 4.52-4.55 (m, 2 H), 7.05 (d, 2 H), 7.22-7.32 (m, 5 H), 7.95 (d, 2 H).

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7fd3e3e7b13040898bfef90e0de46d2e
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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