Triethylamine → Ethyl 2-[4-[4-hydroxy-5-(2-isopropylphenyl)sulfanyl-6-oxo-pyran-2-yl]phenoxy]acetate

HRID 613128Notes

Reaction equation

HRID 613128 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(N(CC)CC)C.[CH:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45][CH:46]([C:50](O)=[O:51])[C:47](O)=[O:48])([CH3:38])[CH3:37]>C(Cl)Cl>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][O:8][C:7]1[CH:15]=[CH:16][C:4]([C:1]2[O:3][C:47](=[O:48])[C:46]([S:45][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[CH:36]([CH3:37])[CH3:38])=[C:50]([OH:51])[CH:2]=2)=[CH:5][CH:6]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 182681Ethyl 2-(4-acetylphenoxy)acetateHCID 19596178[(2-Isopropylphenyl)thio)propanedioic acid

Product 1

HCID 54690953Ethyl 2-[4-[4-hydroxy-5-(2-isopropylphenyl)sulfanyl-6-oxo-pyran-2-yl]phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using ethyl (4-acetyl-phenoxy)acetate (2.14 g, 9.67 mmol), trimethylsilyl triflate (4.48 mL, 23.20 mmol), triethylamine (12.93 mL, 38.6 mmol), methylene chloride (20 mL), and diethyl ester of [(2-isopropylphenyl)thio]propanedioic acid (2.00 g, 6.45 mmol) m.p. 194-196° C.; ; 1H NMR (400 MHz, DMSO-d6) δ 1.57 (m, 9H), 3.41 (m, 1H), 4.81 (q, 2H), 4.89 (s, 2H), 6.75 (s, 1H), 6.90 (d, 1H), 7.05 (m, 4H), 7.26 (d, 1H), 7.79 (d, 2H).

Sources & evidence

ORD record
ord-c42fe3deed5941c49292bd88cfe161e8
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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