Triethylamine → 4-Hydroxy-3-(2-isopropylphenyl)sulfanyl-6-[4-(3-pyridylmethoxy)phenyl]pyran-2-one

HRID 2394049Notes

Reaction equation

HRID 2394049 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH:2]=1.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(N(CC)CC)C.[CH:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[S:46][CH:47]([C:51](O)=[O:52])[C:48](O)=[O:49])([CH3:39])[CH3:38]>C(Cl)Cl>[OH:52][C:51]1[CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:10][CH:11]=2)[O:17][C:48](=[O:49])[C:47]=1[S:46][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[CH:37]([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 19596178[(2-Isopropylphenyl)thio)propanedioic acidHCID 195962674'-(3-Pyridinylmethoxy)acetophenone

Product 1

HCID 546812634-Hydroxy-3-(2-isopropylphenyl)sulfanyl-6-[4-(3-pyridylmethoxy)phenyl]pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 4'-(pyridin-3-ylmethoxy)acetophenone (1.09 g, 4.83 mmol), trimethylsilyl triflate (1.12 mL, 5.79 mmol), triethylamine (1.34 mL, 9.66 mmol), methylene chloride (17 mL), and diethyl ester of [(2-isopropylphenyl)thio]-propanedioic acid (1.00 g, 3.22 mmol) m.p. 225° C.; ; 1H NMR (400 MHz, DMSO-d6) δ 1.23 (d, 6H), 3.41 (m, 1H), 5.26 (s, 2H), 6.78 (s, 1H), 6.90 (d, 1H), 7.08 (dt, 2H), 7.21 (d, 2H), 7.29 (d, 1H), 7.45 (dd, 1H), 7.82 (d, 2H), 7.91 (d, 1H), 8.56 (d, 1H), 8.71 (s, 1H).

Sources & evidence

ORD record
ord-1b53c5e5fc6c4148993161893528d2c9
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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