Triethylamine → HCID 54681307, compound

HRID 613116Notes

Reaction equation

HRID 613116 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[O:5][C:4](=[O:19])[C:3]=1[S:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:27]OC(=O)COC1C=CC(C(=O)C)=CC=1.C(N(CC)CC)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.S1C=CC=C1C(C(OCC)=O)C(OCC)=O>ClCCl>[OH:1][C:2]1[C:7]([CH3:27])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:17][CH:18]=2)[O:5][C:4](=[O:19])[C:3]=1[S:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 241889Methyl (4-acetylphenoxy)acetateHCID 15591544Diethyl (thiophen-2-yl)propanedioateHCID 54681487HCID 54681487, compound

Product 1

HCID 54681307HCID 54681307, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (0.691 g, m.p. 194 - 197° C.) was prepared in a similar manner to that demonstrated in the preparation of [4-[4-hydroxy-2-oxo-3- (phenylthio) -2H-pyran-6-yl]phenoxy]-acetic acid using the following: Methyl-[4-(1-oxoethyl)phenoxy]-acetate (2.00 g, 8.81 mmol), triethylamine (3.68 mL, 26.4 mmol), trimethylsilyltriflate (2.38 mL, 12.3 mmol), dichoromethane (20.0 mL), diethyl 2-(thiophenyl)propane-1,3-dioate (1.34 g, 5.00 mmol.), 1H NMR (400 MHz, DMSO-d6) δ7.585 (d, 2 H, J=9 Hz), 7.325-7.286 (m, 2 H), 7.178 (d, 3 H, J=7.5 Hz), 7.063 (d, 2 H, J=9 Hz), 4.784 (s, 2 H), 2.042 (s, 3 H).

Sources & evidence

ORD record
ord-68e6809072e444c9935ab3be6384ec59
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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